instruction stringlengths 151 5.17k | output stringlengths 291 4.64k |
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Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 100 mg of 3-{4-[4-(3-hydroxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one in 1 mL of dimethylformamide at 0° C. were added 0.077 mL ... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-{4-[4-(3-hydroxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 2-(2-aminopyridin-4-yl)-4-chlorophenol (110 mg, 0.5 mmol), (S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide (122 mg, 0.5 mmol), CuI (10 mg, 0.05 mmol) and Cs2CO3 (191 mg... | {"inputs": {"m1_m2_m6_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(2-aminopyridin-4-yl)-4-chlorophenol"}], "amount": {"mass": {"value": 110.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(S)-6-((1-amino-1-oxopropan-2-yl)amino)-2-chloropyrim... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared and identified by the procedures in Example 12 except that the furandione reactant here used was the tri-n-butylphosphoranylidene dihydro-2,5-furandione from Example 1 and HC... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "furandione"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "tri-n-butylphosphorany... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
0.24 mL of 2.0 mol/L aqueous sodium hydroxide was added dropwise to a mixed solution of 1 mL of methanol and 2 mL of tetrahydrofuran containing 0.13 g of methyl 2-(benzamido)-4-(phenylethynyl)benzoate at ro... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 0.24, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "r... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared as described in Example 7 using (1S,2R)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-phenylpropan-2-amine (1a, 149 mg, 0.41 mmol) and 2-chloro-2-oxoethyl acetate (49 μL, 0.45 mmol). Yield 125 mg (... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(1S,2R)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-phenylpropan-2-amine"}], "amount": {"mass": {"value": 149.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chl... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Combine methyl 2-methoxy-5-(4H-triazol-4-yl)benzoate (56 mmol) and methanol (200 mL) and water (50 mL). Add 1M aqueous solution of sodium hydroxide (62.5 mL, 62.5 mmol). Heat to reflux. After 8 hour, concen... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-methoxy-5-(4H-triazol-4-yl)benzoate"}], "amount": {"moles": {"value": 56.0, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To as solution of 2,2-Difluoro-1-{(4S,5R)-4-fluoromethyl-2,2-dimethyl-5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazolidin-3-yl}-ethanone (200 mg, 0.48 mmol) in toluene (3.2 ml) and ethano... | {"inputs": {"m1_m4_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2,2-Difluoro-1-{(4S,5R)-4-fluoromethyl-2,2-dimethyl-5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazolidin-3-yl}-ethanone"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The reaction of 17.0 ml (0.135 mol) dimethylamine solution and 6.8 g ml (0.050 mol) 2-methoxybenzaldehyde in accordance with general synthesis instructions 1 and subsequent reaction with 3.0 ml (0.050 mol) ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "acetyl chloride"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethylamine"}], "amount": {"volume": {"value": 17.0, "unit... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The reaction according to Reference Example 11 was carried out using (2-chloro-3-pyridyl)methyl chloride in lieu of 2,6-dichloro-3-pyridylmethyl chloride to give the title compound as a yellow oil.
### ORD... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(2-chloro-3-pyridyl)methyl chloride"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-dichloro-3-pyridylmethyl chloride"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_ar... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of N-(3-chloro-4-fluorophenyl)-5-[(triisopropylsilyl)oxy]methyl-1,2,3-thia-diazole-4-carbothioamide (0.18 g, 0.00039 mol) in anhydrous DCM (3 mL, 0.04 mol) under N2 was added DIPEA (82 μL, 0.0... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl trifluoromethanesulfonate"}], "amount": {"volume": {"value": 47.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(3-chloro-4-fluorophenyl)-5-[(triisop... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4-[4-(4-chloro-phenyl)-piperidin-4-yl]-benzonitrile was reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole following the procedure set out in Example 1, but using tetrakis(triphenylpho... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-[4-(4-chloro-phenyl)-piperidin-4-yl]-benzonitrile"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole"}], "reaction_role": "REACTANT"}]}, "m3": {"compo... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Molten pyridine hydrochloride (4.1 g, 0.0354 mol) was added to (+)-trans-2-(2-chlorophenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one (0.4 g, 0.0009 mol) and heated at 180° C.... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "pyridine hydrochloride"}], "amount": {"mass": {"value": 4.1, "units... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 5.2 g of benzyl L-leucinate, 4 g of (3RS, 3aRS,4RS,7RS,7aRS) 3-hydroxy-3a,4,7,7a-tetrahydro-1H,3H-4,7-methano-isobenzofuran1-one and 40 ml of anhydrous benzene was refluxed for 90 minutes while... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "benzyl L-leucinate"}], "amount": {"mass": {"value": 5.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-hydroxy-3a,4,7,7a-tetrahydro-1H,3H-4,7-methano-isobenzofuran1-one"}], "reaction_role... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of sodium methoxide (8.86 g, 0.164 mole), and 3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile (Example 37A, 23.1 g, 0.080 mole) in methanol (60 mL) was heated at reflux for 24... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium methoxide"}], "amount": {"mass": {"value": 8.86, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
DMSO was added dropwise to a solution of (47.5 mL) oxalyl chloride (7.5 mL, 15.0 mmol, 2.0 M in methylene chloride) and the resultant reaction mixture was stirred for 10 min at −78° C. 2,6-Dichlorobenzyloxy... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant mixture"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate hexanes"}], "reaction_role": "REACTANT"}]}, "m2_m7": {"components": [{"identifiers": [{"type": "NAME", "valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A suspension of 3-bromo-phenol (5.5 g, 31.8 mmoles), imidazole (4.3 g, 63.6 mmoles) in CH2Cl2 (70 ml) was added dropwise to a solution of tert-butyl-chloro-dimethylsilane (5.3 g, 35 mmoles) in CH2Cl2 (5 ml)... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl-chloro-dimethylsilane"}], "amount": {"mass": {"value": 5.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "re... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of 4-(methylsulfonyl)aniline hydrochloride (6 g, 28.8 mmol) in toluene (150 ml) at 0° C., trimethylaluminum (2M solution in toluene, 21.6 ml, 43.2 mmol) was added over 15 minutes. The reacti... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "trimethylaluminum"}], "a... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 1,1-dimethylethyl{6-phenyl-2-[({4-[({[(pyridin-3-ylmethyl)oxy]carbonyl}amino)methyl]phenyl}carbonyl)amino]pyridin-3-yl}carbamate (25 mg, 0.045 mmol) in ethyl acetate (5 mL) was treated with 4M... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1,1-dimethylethyl{6-phenyl-2-[({4-[({[(pyridin-3-ylmethyl)oxy]carbonyl}amino)methyl]phenyl}carbonyl)amino]pyridin-3-yl}carbamate"}], "amount": {"mass": {"value": 25.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifie... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 2-Methyl-2-propanesulfinamide (1.47 g) and acetone (0.98 ml) in THF (24 ml) chilled to 0° C. was added Ti(OEt)4 (5.36 ml) dropwise over the course of 15 minutes. After being stirred at room... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Methyl-2-propanesulfinamide"}], "amount": {"mass": {"value": 1.47, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetone"}], "amount": {"volume": {"value": 0.98, "units": "MILLILITER"}}, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 43 g (200 mmol) of 4-bromophenylacetic acid and 0.2 g of conc. H2SO4 in 470 ml of ethanol was refluxed for 16 hours. The reaction mixture was cooled to ambient temperature, stirred with 6 g of... | {"inputs": {"m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-bromophenylacetic acid"}], "amount": {"mass": {"value": 43.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "H2SO4"}], "amount": {"mass": {"value": 0.2, "units": "GRAM"}}, "reaction_role":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
0.792 g (3.065 mmol) of a 1:1 mixture trans-(7-amino-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-1-yl)-propan-1-one and trans-(8-amino-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-1-yl)-propan-1-one were... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "trans-(7-amino-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-1-yl)-propan-1-one"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trans-(8-amino-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-1-yl)-propan-1-on... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of (4-Chloro-phenyl)-[2-(3-dimethylamino-propylsulfanyl)-3-methyl-3H-imidazol-4-yl]-methanone (135 mg) in glacial acetic acid (4.00 mL) was added at rt H2O2 (82.0 μL; 30 wt. % in water... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(4-Chloro-phenyl)-[2-(3-dimethylamino-propylsulfanyl)-3-methyl-3H-imidazol-4-yl]-methanone"}], "amount": {"mass": {"value": 135.0... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of Pd(OAc)2 (146 mg, 0.7 mmol) and 1,1-bis(diphenylphosphino)ferrocene (478 mg, 0.9 mmol) in DMF (65 ml) under an argon atmosphere was stirred at 50° for 15 min and cooled to rt. The reaction mixt... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Amino-6-bromopyrazine-2-carboxylic acid methyl ester"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-furanboronic acid"}], "amount": {"mass": {"value... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 3-[4-(4-fluorophenylthio)phenyl]-1H-pyrazole (85 mg, 0.31 mmol) in 1.5 mL glacial acetic acid was treated with a solution of sodium cyanate (31 mg, 0.47 mmol) in 0.5 mL of water. The resulting... | {"inputs": {"m1_m3_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[4-(4-fluorophenylthio)phenyl]-1H-pyrazole"}], "amount": {"mass": {"value": 85.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium cyanate"}], "amount": {"mass": {"value": 31.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of ethyl 3-amino-4,4-dimethylhexanoate, 27a, (0.19 g. 1.00 mmol) and 5-fluoro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p- olylsulfonyl)pyrrolo[2,3-b]pyridine, 25a, (0.54 g, 1.20 mmol)... | {"inputs": {"m1_m2_m3_m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 3-amino-4,4-dimethylhexanoate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "27a"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "5-fluoro-3-(5-fluoro-4-methylsulfi... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2-[(2,5-dichloropyrimidin-4-yl)amino]-N-methylbenzamide (29.7 mg, 0.100 mmol), diethyl(4-aminobenzyl)phosphonate (29.2 mg, 0.120 mmol), TFA (23 uL, 0.30 mmol) and TFE (1.0 mL) was heated at 10... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[(2,5-dichloropyrimidin-4-yl)amino]-N-methylbenzamide"}], "amount": {"mass": {"value": 29.7, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diethyl(4-aminobenzyl)phosphonate"}], "amou... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 3-[2-(2-oxopyrrolidin-3-yl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (740 mg) in N,N-dimethylformamide (5 ml) was added 60% sodium hydride in mineral oil (120 mg) at... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2-bromoacetate"}], "amount": {"volume": {"value": 0.22, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m5_m2_m3": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
As described for example 73c, 6-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid ethyl ester (89 mg, 0.25 mmol) was converted, instead of 6-[(5-methyl-3-phenyl-isoxazo... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "6-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid ethyl ester"}], "amount": {"mass": {"value": 89.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of the product of Example 21 (194.6 mg), piperidine (196 μL), and acetic acid (114 μL) in DCM (5 mL) was treated with sodium triacetoxyborohydride (570 mg). After 16 h, the resulting mixture was ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m6_m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 194.6, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 64 g (350 mmol) sample of 2-bromobenzonitrile (Aldrich) was dissolved in 650 mL of xylene and treated with 22.75 g (350 mmol) of sodium azide and 95 mL (350 mmol) of tributyltin chloride at reflux for 48 ... | {"inputs": {"m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium azide"}], "amount": {"mass": {"value": 22.75, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tributyltin chloride"}], "amount": {"volume": {"value": 95.0, "units": "MILLILITER"}}, "react... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
70.7 g of p-toluidine, cooled with a bath of water and ice, are treated with 205 ml of 36% HCl. The mixture is then stirred at 55°-60° C. for 30 min before being cooled to 0° C. again. A solution of 45 g of... | {"inputs": {"m1_m9": {"components": [{"identifiers": [{"type": "NAME", "value": "p-toluidine"}], "amount": {"mass": {"value": 70.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 1.74 g, 3-ethyl-2-oximino-4-thiazolidinone in 25 ml of dioxane cooled to 20°C was added to a solution 2.53 g of N-methyl-N-(trichloromethanesulfenyl) carbamyl fluoride in 25 ml dioxane. To ... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-ethyl-2-oximino-4-thiazolidinone"}], "reaction_role": "REACTANT"}, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To sodium hydride (60% dispersion) (1.885 g, 47.1 mmol), was added DMSO (20 mL). The mixture was stirred for 5 min, then diethyl malonate (7.15 mL, 47.1 mmol) was added. The reaction mixture was stirred at ... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl malonate"}], "amount": {"volume": {"value": 7.15, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {"value": 1.885, "un... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-(3-(2-Phenoxyphenyl)-4,5-dihydroisoxazol-5-yl)propanal (38.0 mg, 0.122 mmol), 1-(4-fluorophenyl)piperazine (20.0 mg, 0.111 mmol), molecular sieve (5 beads) and NaBH(OAc)3 (70.5 mg, 0.333mmol) were reacted... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(3-(2-Phenoxyphenyl)-4,5-dihydroisoxazol-5-yl)propanal"}], "amount": {"mass": {"value": 38.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-(4-fluorophenyl)piperazine"}], "amoun... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a similar fashion using route 27 general procedure 70, (8-amino-quinolin-7-yl)-(6-trifluoromethyl-pyridin-3-yl)-methanone (Intermediate 371) (100 mg, 0.32 mmol), N-methylsulfamoyl chloride (Intermediate ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 213"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared according to procedure N by stirring 6′-bromo-1′-(8-chloro-2,3-dimethylquinolin-4-yl)-1′,2,2′,3,5,6-hexahydrospiro[pyran-4,3′-pyrrolo[3,2-b]-pyridine] (25 mg, 0.054 mmol), morpholine (4.75 μL, 0.05... | {"inputs": {"m1_m2_m5_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "6\u2032-bromo-1\u2032-(8-chloro-2,3-dimethylquinolin-4-yl)-1\u2032,2,2\u2032,3,5,6-hexahydrospiro[pyran-4,3\u2032-pyrrolo[3,2-b]-pyridine]"}], "amount": {"mass": {"value": 25.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2.0 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 1.3 g of 60% sodium hydride and 30 mL of N,N-dimethylformamide at room temperature. After the reaction mixture was stirred for 30 minut... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-1-propanol"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"ident... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 80 mg (0.25 mmol) 6-chloro-2-ethylamino-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide and 433 mg (5.0 mmol) morpholine was heated in the microwave to 120° C. for 10 h. A... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "6-chloro-2-ethylamino-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide"}], "amount": {"mass": {"value": 80.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "morpholine... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-(4-phenoxyphenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Compound 2) (199 mg, 0.515 mmol), 1-methyl-4-piperidone(70 ul, 0.566 mmol), sodium triacetoxyborohydride (163 mg, 0.772 mmol) and gla... | {"inputs": {"m1_m2_m3_m4_m5_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(4-phenoxyphenyl)-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine"}], "amount": {"mass": {"value": 199.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Compound 2"}], "r... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared according to the procedure described in Example 131, Step 2, using the following starting materials: (2′-aminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester, N-ethyl-N-... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(2\u2032-aminomethyl-6-methoxy-4\u2032-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-ethyl-N-benzylcarbamoyl chloride"}], "react... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A stream of hydrochloric acid is passed into a suspension of 3.3 g (13.2 mmol) of 1-carboxy-5,6-dihydro-4H-thieno[3,4-c]pyrrole hydrobromide in 75 ml of ethanol, heated at reflux for 4 h. The solvent is the... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-carboxy-5,6-dihydro-4H-thieno[3,4-c]pyrrole hydrobromide"}], "amount": {"mass": {"value": 3.3, "units": "GRAM"}}, "reaction_role": "REACTA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The mixture of 11.2 g of 7-(4-hydroxyphenyl)-7-phenylhexahydro-1,4-oxazepine hydrochloride, 110 ml of dry acetonitrile. 14.0 g of triethylamine and 5.05 g of allyl bromide is stirred at room temperature for... | {"inputs": {"m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "allyl bromide"}], "amount": {"mass": {"value": 5.05, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"mass": {"value": 14.0, "units": "GRAM"}}, "reaction_role": "SOL... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 1(4-aminophenyl)-3-(3-pyridyl)-5-ethylpyrazole (300 mg, 1.14 mmol) and 2-chloro-6-fluorobenzaldehyde (360 mg, 2.27 mmol) in 5% HOAc/MeOH (6 mL) at room temperature under argon was a... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1(4-aminophenyl)-3-(3-pyridyl)-5-ethylpyrazole"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-chloro-6-fluorobenzaldehyde"}], "amount": {"ma... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
n-Butyllithium (1.6 M solution in hexane, 26 ml, 41.6 mmol) was added to a solution of triphenyl-(3,3,3-trifluoro-propyl)-phosphonium iodide (20.25 g, 41.64 mmol) in THF (141 ml) at −78° C. over 13 minutes,... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "n-Butyllithium"}], "amount": {"volume": {"value": 26.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"ide... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4-[3-[2-(cyclopentylamino)-4-pyrimidinyl]-7-(cyclopropylamino)pyrazolo[1,5-a]pyridin-2-yl]phenol (146 mg, 0.34 mmol) in N,N-dimethylformamide (3 mL) was added cesium carbonate (0.22 g, 0.68... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-[3-[2-(cyclopentylamino)-4-pyrimidinyl]-7-(cyclopropylamino)pyrazolo[1,5-a]pyridin-2-yl]phenol"}], "amount": {"mass": {"value": 146.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared using 5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid [prepared from 3-(trifluoromethoxy)benzyl bromide and ethyl 5-cyanoindole-2-carboxylate] and 2-amino-1-... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-1-butanol"}], "reaction_role": "REACTANT"}]}}, "conditions": {"cond... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt (17 mg, 0.039 mmol), 4-fluorobenzonitrile (7.1 mg, 0.058 mmol) and 4-methylmorpholine (13 μL, 0.12 mm... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt"}], "amount": {"mass": {"value": 17.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-fl... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Vanillyl alcohol (5) (10.3 g, 66.8 mmol) was dissolved in ethyl acetate (160 ml) at room temperature, Novozym 435 (2.00 g) was added, and the mixture was stirred at 65° C. for 69 hours. Then, the reaction m... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Vanillyl alcohol"}], "amount": {"mass": {"value": 10.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 160.0, "units": "MILLILITER"}}, "reaction... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Decene-1 23.0 g and maleic anhydride 15.7 g were added thereto and dissolved. Toluene 30 ml dissolving azobisisobutyronitrile 1 g was added in 3 hours. After adding, they were reacted at the same temperatur... | {"inputs": {"m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "azobisisobutyronitrile"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Toluene"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_r... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 3.8 ml of N,N-dimethylformamide was added dropwise 4.2 ml of phosphorus oxychloride at room temperature, and the mixture was stirred at room temperature for 30 minutes. Thereto 1.6 g of 3-chloro-2-(1H-py... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "reaction_role": "REACTANT"}]}, "m5_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "phosphorus oxychloride"}], "amount": {"volume": {"value": 4.2, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
7,8-Methylenedioxy-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylic acid (200 mg, 0.687 mmol) was dissolved in 5 ml of dimethyl formaide, then 152 mg of anhydrous potassium carbonate (1.1 mmol) a... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "7,8-Methylenedioxy-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylic acid"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "va... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
30 ml of thionyl chloride were poured over 15 gm of N-(1-hydroxy-2,2,3-trichloro-n-propyl)-acetamide, and the mixture was refluxed until the solution became clear. Subsequently, the excess thionyl chloride ... | {"inputs": {"m2_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(1-hydroxy-2,2,3-trichloro-n-propyl)-acetamide"}], "amount": {"mass": {"value": 15.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "thionyl chloride"}], "amount": {"volume": {"value": 30.0, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Dissolved methyl 2-[6, 11-dihydro-dibenzo[b,e]oxepin-11-yl]-pent-4-enoate (9.00 g, 0.0292 mol) in 100 mL of dry THF, and cooled to 0° C. under a nitrogen atmosphere. Added 1.0M lithium aluminum hydride in T... | {"inputs": {"m2_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "lithium aluminum hydride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 29.2, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m6": {"components": [{"identifi... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 8-methyl-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-8-ol (Intermediate G) (290 mg, 0.840 mmol) in DCE (10 ml) was added ethyl 7-oxoheptanoate (434 mg, 2.52 mmol) followed by sodi... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium triacetoxyborohydride"}], "amount": {"mass": {"value": 534.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m1_m2_m6... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A reaction mixture of 4-(hydroxymethyl)-quinoline hydrobromide (2.0 g, 12.6mmol) and thionylchloride (20 mL) was heated to reflux for 2 hours. This was allowed to cool and then concentrated in vacuum. The g... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(hydroxymethyl)-quinoline hydrobromide"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "thionylchloride"}], "amount": {"volume": {"value": 20.0, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound is prepared as an off-white lyophilizated powder following Scheme 1 and in analogy to Example 1 using 2-chloro-7-methoxy-quinoxaline, 3-bromo-1,1,1-trifluoro-2-propanol, piperidin-4-yl-ca... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-7-methoxy-quinoxaline"}], "reaction_role": "REACTANT"}]}, "m2": {"compone... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2-chloro-4-((6-nitropyridin-3-yl)oxy)pyridine (20.0 g, 79 mmol) in MeOH (40 mL) was hydrogenated in presence of Raney Nickel (2.00 g, 34.1 mmol) at 40 psi for 3 h. The catalyst was removed via... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-4-((6-nitropyridin-3-yl)oxy)pyridine"}], "amount": {"mass": {"value": 20.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "amount": {"volume": {"value": 40.0, "units": "MI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound, MS: m/e=412.3 (M+H+), was prepared in accordance with the general method of example 2, step 1 and step 2 from 4-chloro-7-iodo-2-methyl-thiazolo[4,5-c]pyridine (Example B), (3-methylsulfo... | {"inputs": {"m0_m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-7-iodo-2-methyl-thiazolo[4,5-c]pyridine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(3-methylsulfonylphenyl)boronic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(E)-5-Bromo-1-(3,4,5-trimethoxyphenyl)-1-pentene (434 mg) and homopiperazine (276 mg) were reacted in the same manner as in Preparation Example 4 to obtain the title compound.
### ORD JSON:
| {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(E)-5-Bromo-1-(3,4,5-trimethoxyphenyl)-1-pentene"}], "amount": {"mass": {"value": 434.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "homopiperazine"}], "amount": {"mass": {"value": 276.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 4-(1H-benzoimidazol-2-ylsulfanyl)-5-(1H-benzoimidazol-2-ylsulfanylmethyl)-3-hydroxy-5-hydroxymethyl-5H-furan-2-one (220 mg, 0.50 mmol), dimethylaminoacetyl chloride hydrochloride (174 mg, 1.10... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(1H-benzoimidazol-2-ylsulfanyl)-5-(1H-benzoimidazol-2-ylsulfanylmethyl)-3-hydroxy-5-hydroxymethyl-5H-furan-2-one"}], "amount": {"mass": {"value": 220.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-Hydroxypyrazine-2-carboxylic acid is converted to the methyl ester and the ester is reduced with lithium aluminium hydride in tetrahydrofuran to give 3-hydroxy-2-hydroxymethylpyrazine. Treatment of 3-hydr... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "lithium aluminium hydride"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Hydroxypyrazine-2-carboxylic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"t... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of tridecanoic acid, methyl ester (24.63 g, 0.1078 mol), and anhydrous hydrazine (3.40 mL, 0.108 mol) in absolute ethanol (150 mL) was stirred at room temperature for 24 hours, then refluxed 2 da... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "tridecanoic acid, methyl ester"}], "amount": {"mass": {"value": 24.63, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrazine"}], "amount": {"volume": {"value": 3.4, "units": "MILLILITER"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 1-methyl-1H-pyrazol-3-amine (223 mg) in cyclopentyl methyl ether (5.0 mL) was added ethyl 1-cyanocyclopropanecarboxylate (0.90 ml). The reaction mixture was stirred at 120° C. for 30 hr, an... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-methyl-1H-pyrazol-3-amine"}], "amount": {"mass": {"value": 223.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide (may be prepared as described in Description 37) (31 mg, 0.12 mmol) in dichloromethane (3 ml) was added cyclopentanone (20 mg, ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclopentanone"}], "reaction_role": "REACTANT"}]}, "m1_m6_m2_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzamide"}], "amount": {"mass": {"value": 31.0, "units": "MILLI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
SOCl2 (0.5 mL) is added to a solution of 4-[6-(2,6-diethyl-phenyl)-4-methoxy-pyridin-3-yl]-heptan-4-ol in anhydrous pyridine (5 mL) at 0° C. under nitrogen. The resulting mixture is stirred at room temperat... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "SOCl2"}], "amount": {"volume": {"value": 0.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-[6-(2,6-diethyl-phenyl)-4-methoxy-pyridin-3-yl]-heptan-4-ol"}], "reaction_role": "REACTAN... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared from (2-amino-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example J3) (207 mg, 0.75 mmol) and 3-[3-(2-methyl-pyridin-3-yl)-phenyl]-3-oxo-propionic acid tert-but... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(2-amino-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester"}], "amount": {"mass": {"value": 207.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[3-(2-methyl... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 2.16 parts of 1H-1,2,4-triazol-5-thiol, 1.03 parts of a sodium hydride dispersion 50% and 18 parts of methylbenzene was stirred for 3 hours at room temperature. A solution of 6.3 parts of cis-1... | {"inputs": {"m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1H-1,2,4-triazol-5-thiol"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methylbenzene"}], "reaction_role": "SOLV... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Synthesized from pivalic acid 6-{2-[ethyl(4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (29 mg) and 2-chloro-1-piperidin-1-ylpropan-1-one (20 mg) according to an analogous... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "pivalic acid 6-{2-[ethyl(4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester"}], "amount": {"mass": {"value": 29.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In substantially the same manner as in Reference Example 31, isobutyramide was allowed to react with 1,3-dichloroacetone to give 4-chloromethyl-2-isopropyl oxazole as an oily product. The yield was 6.2%.
#... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "isobutyramide"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1,3-dichloroacetone"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"produc... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of (+) (1S, 2R, 3S)-3-(2-carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid in absolute ethanol/water (12 to 1) was titrated to pH=11-12 with 1.... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(+) (1S, 2R, 3S)-3-(2-carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
135 mg 2-{[1-(1-Benzothiazol-2-yl-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester in 1 ml methanol and 1.5 ml 1M aqueous sodium hydroxide solution were heated to 100° C. for 2 mi... | {"inputs": {"m1_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-{[1-(1-Benzothiazol-2-yl-ethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester"}], "amount": {"mass": {"value": 135.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
This compound was prepared by using procedures analogous to those described for the synthesis of Example 50B starting from 5-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydro... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}pyridine-2-carboxylic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "azetidine-3-c... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 4-aminophenylacetonitrile (20 g, 151.3 mmol) in dry DMF (150 ml) was treated with potassium carbonate (50.1 g, 363.1 mmol), benzyl bromide (54.4 g, 318 mmol), and potassium iodide (5 g, 0.2 30... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m5_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-aminophenylacetonitrile"}], "amount": {"mass": {"value": 2... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Using the same general procedure as used for the synthesis of 1H-pyrrole-2-carboxylic acid [3-(2-amino-1H-imidazol-4-yl)-propyl]-amide hydrochloride 17, 0.200 g of 4-(3-amino-propyl)-1H-imidazol-2 -ylamine ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1H-pyrrole-2-carboxylic acid [3-(2-amino-1H-imidazol-4-yl)-propyl]-amide hydrochloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-(3-amino-propyl)-1H-imidazol-2 -ylamine dihydrochloride"}], "amount": {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a flask containing 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.6 g, 6.96 mmol), the product of Step 2 (2.52 g, 6.96 mmol), dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosp... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline"}], "amount": {"mass": {"value": 1.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3_m5_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "a... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred mixture of 67.7 parts of 2-amino-5-(2-hydroxyethyl)-6-methyl-4(3H)-pyrimidinone and 800 parts of ethanol were added 80 parts of a sodium methoxide solution 30%. The reaction mixture was heated ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium methoxide"}], "reaction_role": "REACTANT"}]}, "m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "67.7"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-amino-5-(2-hydroxyethyl)-6-methy... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Compound #16 N-(2-amino-6-fluorobenzyl)-2-[1,6]naphthyridinecarboxamide To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol) in anhydrous DMF (1.0 mL) at room temperature was add... | {"inputs": {"m1_m2_m3_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "Compound #16"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-(2-amino-6-fluorobenzyl)-2-[1,6]naphthyridinecarboxamide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-[1,... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Under argon atmosphere, a solution of ethyl 7-bromo-2,3-dihydro-1-benzoxepine-4-carboxylate (1.0 g), 4-methylthiophenyl borate (622 mg) and potassium carbonate (0.93 g) in toluene-ethanol-water (30-3-3 ml) ... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrakistriphenyl-phosphinepalladium"}], "amount": {"mass": {"value": 0.13, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 7-bromo-2,3-dihydro-1-benzoxepine-... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 5-((2-chloro-6-fluorobenzyl)thio)-4-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-ol (50 mg, 0.124 mmol), 2-chloro-6-fluorobenzyl bromide (39 mg, 0.175 mg), and sodium methoxide (18 mg, 0.33 m... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "5-((2-chloro-6-fluorobenzyl)thio)-4-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-ol"}], "amount": {"mass": {"value": 50.0, "u... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4 equivalents of ozone are introduced over a period of 60 minutes into a solution, cooled to -15°, of 150 mg of 2-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-3-methylcrotonic acid methyl ester in 3 ml of methano... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ozone"}], "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-3-methylcrotonic acid methyl ester"}], "amount": {"mass": {"value": 150.0, "units": "MILLI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared starting from 100 mg (0.187 mmoles) of 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide (WO 2005/002577), 79 mg... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "cesium carbonate"}], "amount": {"mass": {"value": 112.4, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "copper iodide"}], "amount": {"mass": {"value": 72.0, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of N-(5-bromothiophene-2-sulfonyl)pyrrole (600 mg, 2.05 mmol), 3,3-dimethyl-1-butyne (338 mg, 4.1 mmol), copper iodide (39 mg, 0.21 mmol), tetrakistriphenylphosphine palladium [Pd(PPh3)4] (118 mg,... | {"inputs": {"m1_m2_m6_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(5-bromothiophene-2-sulfonyl)pyrrole"}], "amount": {"mass": {"value": 600.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3,3-dimethyl-1-butyne"}], "amount": {"mass": {"value"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of N-methyl-N-{2-[5-(2-oxo-2-thiomorpholinoethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide (560 mg) in tetrahydrofuran (15 mL), ethanol (5 mL) and water (5 mL) was a... | {"inputs": {"m1_m6_m7_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-methyl-N-{2-[5-(2-oxo-2-thiomorpholinoethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}thiophene-2-sulfonamide"}], "amount": {"mass": {"value": 560.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"ty... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a 0° C. solution of methyl 2-[1-(2-hydroxyethyl)-1H-imidazol-4-yl]pyridine-4-carboxylate (500 mg, 2 mmol) in DCM (10 mL) was added TEA (255 mg, 2.5 mmol) followed by drop-wise addition of a solution of m... | {"inputs": {"m8": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m6_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-[1-(2-hydroxyethyl)-1H-imidazol-4-yl]pyridine-4-carboxylate"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2,2-Dimethyl-5-methoxy-7-n-pentyl-4-(4-pyridyl)-2H-chromene (3.90g.) was hydrogenated for 4.5 hours at 20° C and 30 p.s.i. in ethanol (100 ml) in the presence of 5% palladium on charcoal (0.50g.). The solut... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,2-Dimethyl-5-methoxy-7-n-pentyl-4-(4-pyridyl)-2H-chromene"}], "amount": {"mass": {"value": 3.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"vol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Methylsulfonyl-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine from Reference Example 3 was reacted with 3-fluorophenol according to the procedure described in Example 74 to afford 2-(3-fluorophenylox... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Methylsulfonyl-4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyrimidine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-fluorophenol"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 6-chloro-2-methoxycarbonyl-1-(4-fluorophenyl)-3-indolinon (7.5 g)in NMP (75 ml) was added MgCl2, 6H2O (9 g). The mixture was heated at 130° C. under N2 for one hour and finally the temperature was raised... | {"inputs": {"m1_m6_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "6-chloro-2-methoxycarbonyl-1-(4-fluorophenyl)-3-indolinon"}], "amount": {"mass": {"value": 7.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MgCl2"}], "reaction_role": "REACTANT"}, {"ident... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 1,2,3,4-tetrahydro-isoquinolin-5-ylamine 24a (3.83 g, 25.84 mmol) and 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (5.9 g, 24.54 mmol) in methoxyethanol (60 mL) was heated to 60° C. with stirr... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1,2,3,4-tetrahydro-isoquinolin-5-ylamine"}], "amount": {"mass": {"value": 3.83, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-chloro-6,7-dimethoxy-3H-quinazolin-4-one"}], "amount": {"mass... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 12.4 g p-tolunitrile in 500 mL of diethyl ether was added 23 g of solid lithium bis(trimethylsilyl)amide at ambient temperature. The mixture was stirred for 2 hours then hydrolysed with 10%... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "p-tolunitrile"}], "amount": {"mass": {"value": 12.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 2 L metal reactor was charged with [2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester (65 g, 181.4 mmol) in ethanol (1.3 L) was added Pt(IV)O2 (6.5 g). The reactor was evacuated, purged with N2(... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "[2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester"}], "amount": {"mass": {"value": 65.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 1.3... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a 10 L-reaction flask, 594 g (1.92 mol) of 3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl) propionitrile and 6000 g of tetrahydrofuran were added, 214 g (2.11 mol) of triethyl amine was adde... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-oxo-2-(4-tert-butylphenyl)-3-(1,3,4-trimethylpyrazol-5-yl) propionitrile"}], "amount": {"mass": {"value": 594.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 1.2 g of 5-chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[5,4-d]pyrimidine in 42 ml of dichloromethane was cooled to 0° C., and 10 ml of a 1 M solution of boron tribromide in dichloromethane w... | {"inputs": {"m1_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "5-chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[5,4-d]pyrimidine"}], "amount": {"mass": {"value": 1.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of [3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester (0.5 g, 1.04 mmol) and Mo(CO)6 (3.0 g, 0.01 mmol) in Acetonitrile (50 mL) and water (... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "[3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2-methyl-3-methylsulfanyl-2H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxide (0.5 g) and benzylamine (0.5 mL) in dioxane (2.5 mL) was refluxed until completion of the reaction (t.l.c.). After cool... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-methyl-3-methylsulfanyl-2H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxide"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzylamine"}], "amount": {"volu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of methyl 5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylate (Compound E18, 300.0 mg, 0.926 mmol) in 4.0 mL of EtOH and 2.0 mL TBH was added NaOH (200.0 mg, 5.00 mmol; 5.0 nmL o... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "aqueous solution"}], "reaction_role": "REACTANT"}]}, "m1_m2_m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylate"}], "amount": {"mass": {"value": 300.0, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4′-({2-ethyl-1-[4-(2-hydroxy-1,1-dimethylethoxy)phenyl]-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl}methyl)biphenyl-2-carbonitrile (0.49 g) and 2,6-lutidine (0.33 mL) in dichloromethane (10 mL... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4\u2032-({2-ethyl-1-[4-(2-hydroxy-1,1-dimethylethoxy)phenyl]-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl}methyl)biphenyl-2-carbonitrile"}], "amount": {"mass": {"value": 0.49, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifier... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.233 g, 0.571) and ethyl formate (0.140 mL, 1.71 mmol) were dissolved in anhydrous ethanol (1.... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide"}], "amount": {"mass... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 12.7 g of 1-acetyl-4-(5-fluoro-2-hydroxybenzoyl)-piperidine, 6.6 g of hydroxylamine hydrochloride, 11.0 g of ammonium acetate and 200 ml of ethanol-ether was heated under reflux for 10 hrs. Aft... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclohexane"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-ace... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
One molar equivalent (2.24 g) of 4-hydroxy-3-nitrobenzene sulfonic acid sodium salt (HNSA) was mixed together with one molar equivalent (2.06 g) of dicyclohexylcarbodiimide and one molar equivalent (2.10 g)... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-hydroxy-3-nitrobenzene sulfonic acid sodium salt"}], "amount": {"mass": {"value": 2.24, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dicyclohexylcarbodiimide"}], "amount": {"mass": {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred mixture of 2-methylquinolin-7-ol (300 mg, 1.88 mmol), Cs2CO3 (1.84 g, 5.65 mmol) and NMP (10 mL) was added 1-bromo-2-methoxyethane (0.786 g, 5.65 mmol). The reaction mixture was stirred at ambi... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-methylquinolin-7-ol"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Cs2CO3"}], "amount": {"mass": {"value": 1.84, "units": "GRAM"}}, "reaction_r... |
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