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:
3-(R)-(-)-(1-cyano-1,1-diphenylmethyl)pyrrolidine (9.2 g--see Preparation 9(B)) was dissolved in 95% sulphuric acid (80 ml) and the mixture was heated at 80° C. for 4 hours and then at 90° C. for 1 hour. Ic... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"mass": {"value": 120.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 4-tert-butyl-N-{5-(4-methylphenyl)-6-[2-(4-nitrophenoxy)ethoxy]pyrimidin-4-yl}benzenesulfonamide (383 mg), 10% palladium-carbon (50 mg) and ethanol-tetrahydrofuran (6 ml-3 ml) is subjected to c... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-tert-butyl-N-{5-(4-methylphenyl)-6-[2-(4-nitrophenoxy)ethoxy]pyrimidin-4-yl}benzenesulfonamide"}], "amount": {"mass": {"value": 383.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "p... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of bromoform (0.94 mL, 10.8 mmol) in 5 mL of dichloromethane was added over 1.5 hours to a stirred solution of benzyl 3-pyrroline-1-carboxylate (1.77 mL, 9.8 mmol) and benzyltriethylammonium chlo... | {"inputs": {"m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "H2O"}], "reaction_role": "SOLVENT"}]}, "m1_m3_m2_m4_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "bromoform"}], "amount": {"vol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-(5-Chloro-1H-benzimidazol-2-yl thio)nitrobenzene (0.3 g) was dissolved in dry ethanol (100 ml) with warming and the solution was hydrogenated in the presence of 10% Pd/C at 3 atmospheres pressure and 50° ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(5-Chloro-1H-benzimidazol-2-yl thio)nitrobenzene"}], "amount": {"mass": {"value": 0.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 100.0, "units"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Toluene (0.7 ml) and a saturated aqueous sodium hydrogencarbonate solution (0.35 ml) were added to 4-(2-iodo-6-methyl-pyridin-3-yloxy)-6,7-dimethoxy-quinoline (compound 116) (50 mg), tetrakistriphenylphosph... | {"inputs": {"m7": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m4_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Toluene"}], "amount": {"volume": {"value": 0.7, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
843 mg (21 mmol, 55% oily) of sodium hydride was suspended in dimethyl sulfoxide (30 ml). Under ice-cooling, 2.0 ml (16.7 mmol) of benzylmercaptan was added thereto, followed by stirring for 10 minutes. To ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {"value": 843.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"com... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of lithium aluminum hydride (0.73 g, 19.24 mmol, 2.2 equivalents) in anhydrous tetrahydrofuran (20 mL) at 0° C. was added dropwise a solution of (R)-1-(N-benzyloxycarbonylpyrrolidin-2-... | {"inputs": {"m1_m5_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "lithium aluminum hydride"}], "amount": {"mass": {"value": 0.73, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(R)-1-(N-benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene"}], "amount": {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 3-[5-methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propionaldehyde (0.084 g, 0.21 mmol) in CH2Cl2 (0.5 mL) were added 1-piperidin4-yl-... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NaBH(OAc)3"}], "amount": {"mass": {"value": 0.058, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m6_m2_m7_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[5-methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetr... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
199 g (0.91 mol) of 3,3-dimethyl-12-ethyl-1-aza-1,5,9-cyclododecatriene is added dropwise, in the course of 15 minutes, to a solution of 150 g (1.53 mols) of sulphuric acid in one liter of water. Impurities... | {"inputs": {"m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3,3-dimethyl-12-ethyl-1-aza-1,5,9-cyclododecatriene"}], "amount": {"mass": {"value": 199.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sulphuric acid"}], "amount": {"mass": {"value": 150... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Method F2 was used with 8-(4-aminophenoxy)pyrido[2,3-b]pyrazine-2,3(1H,4H)-dione and 4-chloro-3-trifluoromethylphenyl isocyanate to obtain the tithe compound (yield 38%).
### ORD JSON:
| {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "8-(4-aminophenoxy)pyrido[2,3-b]pyrazine-2,3(1H,4H)-dione"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-3-trifluoromethylphenyl isocyanate"}], "reaction_role": "REACTANT"}]}}, "c... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
EDC (0.21 g, 1.08 mmol) was added to a suspension of 3-(6-amino-pyridin-3-yl)-acrylic acid (148 mg, 0.9 mmol), HOBt (134 mg, 1 mmol), (3-chloro-benzofuran-2-ylmethyl)methylamine (194 mg, 0.99 mmol), and (i-... | {"inputs": {"m7": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 32.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m4_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "EDC"}], "amount": {"mass": {"value": 0.21, "units": "GRAM"}}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4 g of product obtained in stage A are heated to reflux for 1 hour with 4 g of sodium acetate in 80 cm3 of acetic anhydride. The mixture is cooled to room temperature and evaporated to dryness, the residue ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium acetate"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "rea... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4-Methoxy-3-morpholin-4-yl-phenylamine (80.0 mg, 0.384 mmol), N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (70.0 mg, 0.192 mmol) and N,N-Diisopropylethylami... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Methoxy-3-morpholin-4-yl-phenylamine"}], "amount": {"mass": {"value": 80.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirring solution of 4-(4-(difluoromethoxy)-2-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one (80 mg, 0.25 mmol) in acetonitrile (10 mL) was added potassium carbonate (104 mg, 0.75 mmol) and follow... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(4-(difluoromethoxy)-2-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one"}], "amount": {"mass": {"value": 80.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}]... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 2-chloro-9-cyclopentyl-7-ethyl-7-fluoro-8,9-dihydro-5H-pyrimido[4,5-b][1,4]diazepin-6(7H)-one (890 mg, 2.85 mmol) in 10 mL of DMA was added sodium hydride (60% dispersion in mineral oil, 11... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-9-cyclopentyl-7-ethyl-7-fluoro-8,9-dihydro-5H-pyrimido[4,5-b][1,4]diazepin-6(7H)-one"}], "amount": {"mass": {"value... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Similar procedure as described in example 384 was used, starting from 1-Isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-6-carboxylic acid and Pyrrolidine to give [1-Isopropoxy-3-(5-methyl-1H-pyraz... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-Isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-6-carboxylic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Pyrrolidine"}], "reaction_role": "REACTANT"}]}}, "conditions":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of iron (III) oxide and molybdenum trioxide (G-105 from Girdler) is used as the catalyst in the reactor described in Example 1 and the temperature of the air bath is adjusted to 225° C. 60 l of ai... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "pantolactone"}], "amount": {"mass": {"value": 33.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "pantolactone"}], "reaction_role": "REACTANT"}]}, "m3_m4": {"components": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Heptylamine (39 g; 0.34 mole was added dropwise to 46.6 g (0.59 mole) of pyridine and 43.4 g (0.43 mole) of acetic anhydride over 30 minutes, and the mixture was further stirred for 2 hours. After the react... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Heptylamine"}], "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"mass": {"value": 46.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "N... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
11.6 g of the 3-(4-chloro-2-fluorophenyl)-5-difluoromethoxy-1H-pyrazole (purity 86%) obtained in step 1.2 were initially charged in 100 ml of toluene. 6.2 g of dimethyl sulfate were added dropwise, and the ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(4-chloro-2-fluorophenyl)-5-difluoromethoxy-1H-pyrazole"}], "amount"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound is prepared from morpholine-4-carboxylic acid [1-(4-cyano-piperidin-4-ylcarbamoyl)-3,3-dimethyl-butyl]-amide hydrochloride and benzyl isocyanate in the presence of a tertiary amine base s... | {"inputs": {"m0_m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "morpholine-4-carboxylic acid [1-(4-cyano-piperidin-4-ylcarbamoyl)-3,3-dimethyl-butyl]-amide hydrochloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzyl isocyanate"}], "reaction_role": "REA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound is prepared from 4-[5-(2-fluoro-4-methanesulfonylmethyl-phenyl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-N-hydroxy-piperidine-1-carboxamidine and isobutyryl chloride following a procedure ana... | {"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-[5-(2-fluoro-4-methanesulfonylmethyl-phenyl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-N-hydroxy-piperidine-1-carboxamidine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "isobutyryl chloride"}], "reaction_rol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of the title G compound, 3-(3-benzyloxy-4-nitro-phenyl)-2-amino-propionic acid methyl ester (597 mg, 1.7 mmol), isatoic anhydride (278 mg, 1.7 mmol) and pyridine (5 mL) is heated with stirring at ... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(3-benzyloxy-4-nitro-phenyl)-2-amino-propionic acid methyl ester"}], "amount": {"mass": {"value": 597.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "isatoic anhydride"}], "amount":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared as in Example 22b from 3-phenoxy-1-propanol and 2-amino-6-fluorobenzonitrile as a yellow oil (93%). 1H NR (400 MHz, DMSO-d6) δ 2.14 (m, 2H), 4.10-4.16 (m, 4H), 5.98 (s, 2H), 6.23 (d, J=8.0 Hz, 1H),... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-phenoxy-1-propanol"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-amino-6-fluorobenzonitrile"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of tert-butyl N-[2-[(4-methylthiazol-2-yl)amino]ethyl]carbamate (435 mg, 1.69 mmol) in acetone (20 mL) was added HCl (4N in dioxane, 2.6 mL, 10.40 mmol) and the reaction mixture was stirred at... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl N-[2-[(4-methylthiazol-2-yl)amino]ethyl]carbamate"}], "amount": {"mass": {"value": 435.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of the product from step 1 (520 mg, 0.73 mmol) in tetrahydrofuran (10 mL) at 5° C. was added ammonium hydroxyde (30%, 2 mL) and the reaction was stirred at 5° C. for 40 minutes. The mixture wa... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl ether"}], "reaction_role": "SOLVENT"}]}, "m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 520.0, "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 mixture of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 1 (0.250 g, 0.905 mmol) in DCM (15.0 mL) were added propanehydrazide 202 (0.120 g, 1.358 mmol), 1-hydroxybenzotria... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM"}], "reaction_role": "SOLVENT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid"}], "amount": {"mass": {"value": 0.25, "units": "GRAM"}}, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
830 g of 3-(1-methylcyclohexen-4-yl)-butyr-aldehyde were dissolved in 800 ml of liquid ammonia in stirrer autoclave and hydrogenated under a hydrogen pressure of 100 bar over 50 g of Raney nickel iron at 90... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogen"}], "reaction_role": "REACTANT"}]}, "m1_m5_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(1-methylcyclohexen-4-yl)-butyr-aldehyde"}], "amount": {"mass": {"value": 830.0, "units": "GRAM"}}, "reaction_role": "REACT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Nα-Cyclohexylcarbonyl-S-benzyl-L-cysteinyl-O-benzyl-L-tyrosyl-O-benzyl-L-serine methyl ester is obtained by reacting Nα-t-butoxycarbonyl-L-serine resin (10 g.) successively with 11.2 g., 30 mmol of Nα-t-but... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclohexane carboxylic acid"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine"}], "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Alternatively, a mixture of hexahydro-1H-1,4-diazepine (17.47 g, 174.4 mmol) and methyl 4-(bromomethyl)benzoate (5.0 g, 21.8 mmol) was heated with triethylamine (24 mL, 174.4 mmol) in tetrahydrofuran (872 m... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "REACTANT"}]}, "m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 24.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identi... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared from (±)-(3SR,3aRS)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid, Example 15 and ethyl glycolate according to Method E. ... | {"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(\u00b1)-(3SR,3aRS)-2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl glycolate"}], "reaction_role": "R... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Into a 500 ml flask was placed 3.0 g of 3-(2-Thienyl)-D,L-alanine (optically active material in the L-form is available 4from Aldrich or SIGMA and could be used to obtain an optically active product) in 75 ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "AcOH CH3CN H2O"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(2-Thienyl)-D,L-alanine"}], "amount": {"mass": {"value": 3.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"co... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a cooled (−78° C.) solution of [2-(3-bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine (400 mg, 1.4 mmol) in anhydrous toluene (16 mL), TMEDA (240 uL, 2.8 mmol) was added followed by nBuLi (1.0 mL, 1.7 ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-fluoro-3-pyridine-carbaldehyde"}], "amount": {"mass": {"value": 0.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "[2-(3-bromo-benzo[b]thiophen-2-yl)-ethyl]-dimeth... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A suspension of 6.0 grams (0.023 mole) of 2,3,5-trichlorophenylacetic acid in about 125 mL of carbon tetrachloride was stirred, and 5 mL of thionyl chloride was added. The reaction mixture was then warmed t... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2,3,5-trichlorophenylacetic acid"}], "amount": {"mass": {"value": 6.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "carbon tetrachloride"}], "amount": {"volume": {"value": 125.0, "units": "MI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Using a procedure analogous to Example 134B, 1-{4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenyl}-4,4-dimethyl-pentan-3-one and NaBH4 give the title compound (quant).
### ORD JSON:
| {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-{4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenyl}-4,4-dimethyl-pentan-3-one"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "NaBH4"}], "reaction_role": "REACTANT"}]}}, "cond... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of tert-butyl 3-bromo-5-formylbenzoate (119 g, 417 mmol) in dioxane (2.4 L) were added hydroxylamine hydrochloride (44.0 g, 633 mmol) and pyridine (103 mL, 1.27 mol). The reaction mixture was ... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl 3-bromo-5-formylbenzoate"}], "amount": {"mass": {"value": 119.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydroxylamine hydrochloride"}], "amount": {"mass": {"value": 44.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Compound 35.17 (15 mg, 0.032 mmol) was suspended in 3 mL water, and treated with 30% hydrogen peroxide (100 mL). The mixture was heated to 90° C. for 3 h and sodium sulfite (113 mg, 0.9 mmol) was added to q... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Compound 35.17"}], "amount": {"mass": {"value": 15.0, "units": "MILLIGRAM"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In the manner given in Example 2, potassium iodide and 8-(methylthio)-1-(chloromethyl)-6-phenyl-4H-s-triazolo-[4,3-a][1,4]benzodiazepine in tetrahydrofuran is treated with propylcyclopropylamine to give 8-(... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium iodide"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "8-(met... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Methyl 6-amino-5-bromonicotinate (500 mg, 2.16 mmol), 2-methoxycarbonylphenylboronic acid (580 mg, 3.25 mmol), palladium(II) acetate (20 mg, 0.09 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (70 m... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m7_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Methyl 6-amino-5-bromonicotinate"}], "amount": {"mass": {"value": 500.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-5-methoxy-1H-isoindol-1-yl)propionaldehyde (0.38 g) was coupled to 4-(2-methylsulfinylphenyl)piperidine (0.29 g) by a method similar to that described in... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(3,4-Dichlorophenyl)-3-(2-methyl-3-oxo-2,3-dihydro-5-methoxy-1H-isoindol-1-yl)propionaldehyde"}], "amount": {"mass": {"value": 0.38, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A stirred solution of 4.10 g of 2-amino-α-(4-methoxyphenyl)-N-methylphenethylamine, 16.22 g of triethyl orthoacetate and 5.6 ml of glacial acetic acid is held under reflux (bath temperature 112° C.) for 2 h... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-\u03b1-(4-methoxyphenyl)-N-methylphenethylamine"}], "amount": {"mass": {"value": 4.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "triethyl orthoacetate"}], "amou... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of MeCN (45 mL), 1-O-acetyl-3,5-di-O-(4-chlorobenzoyl)-2-deoxy-D-ribofuranose (3.0 g), 2-[(trimethylsilyl)amino]4-[(trimethylsilyl)oxy]-s-triazine (1.78 g) and TfOH (0.5 g) were stirred at about 0... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH"}], "reaction_role": "SOLVENT"}]}, "m4_m5_m9": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MeONa"}], "reaction_role": "REACTANT"}, {"i... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 4d (0.81 g, 2.9 mmol), 4-bromo-thiophene-2-carboxylic acid (0.3 g, 1.45 mmol), tetrakis(triphenylphosphine)palladium (80 mg, 0.073 mmol) ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "REACTANT"}]}, "m1_m2_m7_m3_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(2-Methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane"}], "amount": {"mass": {"value": 0.81,... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Under nitrogen atomosphere, 1 ml of trifluoroacetic acid was added slowly to a solution of 500 mg of diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methyl... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "trifluoroacetic acid"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diphenylmethyl 7\u03b2-[2-(2-aminothiazol-4-yl)-2-(Z)-(methoxyimino)aceta... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Aminoacetophenone(5.6 g, 41.5 mmol)and sulfamide (4 g, 41.5 mm) were added to diglyme (70 ml, dried over 4A molecular sieves) and the solution heated under nitrogen at 150° C. After 1 hour a solid forms b... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3,4-Dihydro-4-methyl-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-2,2-dioxide"}], "amount": {"mass": {"value": 2.4, "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:
The title compound was prepared in analogy to the procedure described for Example 25 but 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-ethyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermedi... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-bromo-5-(5-chloro-2-methyl-... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Butyl lithium (BuLi) (5.6 mL, 1.40 equiv) was added dropwise to a solution of 5-bromobenzo[d][1,3]dioxole (2 g, 9.95 mmol, 1.00 equiv) and triisopropyl borate (1.96 g, 14.00 mmol, 1.40 equiv) in THF (20 mL)... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "H2SO4"}], "amount": {"mass": {"value": 4.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Butyl lithium"}], "amount": {"volume": {"value": 5.6, "units": "MILLILIT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 3,5-diiodo-4-(4′-methoxy-3′-iso-propylphenoxy)phenol (0.28 g, 0.55 mmol) in dichloromethane (17.0 mL) at −78° C. was added BBr3 (13.1 mL, 13.1 mmol, 1.0 M solution in CH2Cl2). The r... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3,5-diiodo-4-(4\u2032-methoxy-3\u2032-iso-propylphenoxy)phenol"}], "amount": {"mass": {"value": 0.28, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "BBr3"}], "amount": {"volume": {"value": 1... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A crude reaction mixture originating from the calcium hydroxide-catalyzed Tishchenko reaction of 375 g of hydroxypivalaldehyde and additionally containing 12 g of water, was treated with 10.2 g of glacial a... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"mass": {"value": 120.0, "units": "GRAM"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "calcium hydroxide"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"id... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 300 mg of pyridine were added 120 mg of 5-amino-1- (6-amino-3, 5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, 80 mg of 3-hydroxyaminoazetidine hydrochloride, ... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "5-amino-1- (6-amino-3, 5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydro... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of 5.5 g of NaH (60% dispersion in mineral oil) in 400 ml of dry tetrahydrofuran 7.0 g of 17β-(3-furyl)-5β-androstane-3β,14β-diol (II-a: Ref. comp.) (Minato H. and Nagasaki T., J. Chem. Soc.... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "NaH"}], "amount": {"mass": {"value": 5.5, "units": "GRAM"}}, "reac... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a refluxing solution of 3-pyridinol (9.7 g, 0.10 mol) and triethylamine (17.0 mL, 0.12 mol) in anhydrous benzene (300 mL) was slowly added a solution of N,N-dimethylcarbamyl chloride (14.4 mL, 0.11 mol) ... | {"inputs": {"m1_m2_m4_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3-pyridinol"}], "amount": {"mass": {"value": 9.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 17.0, "units": "MILLILITER"}}, "reacti... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1-(4-hydroxyphenyl)ethanone (8.2 g, 60.2 mmol), potassium carbonate (15.2 g, 110.1 mmol), and KI (1.0 g, 6.0 mmol) in 100 DMF was stirred for 5 min, then 1,2-dibromoethane (60 ml, 696.2 mmol) was added. The... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(4-hydroxyphenyl)ethanone"}], "amount": {"mass": {"value": 8.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 15.2, "units": "GRAM"}},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1-(4-(((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, (1... | {"inputs": {"m0_m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "5,6-dichloropyrimidin-4-amine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert-butyl 4-(aminomethyl)piperidine-1-carboxylate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "va... |
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 Example 5, morpholine (1.41 ml) and Boc-L-Tyr(Bzl)-OH (6.00 g, manufactured by Peptide Institute, Inc.) were condensed to give N-(O-benzyl-Boc-L-tyrosyl)morpholine (8.... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "morpholine"}], "amount": {"volume": {"value": 1.41, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Boc-L-Tyr(Bzl)-OH"}], "amount": {"mass": {"value": 6.0, "units": "G... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Three g of the product of Example 65 was reacted with 1.1 g of cyclopropylamine, substantially as shown in Example 60, to obtain 2.6 g of the desired product, m.p. 175°-177°.
### ORD JSON:
| {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "cyclopropylamine"}], "amount": {"mass": {"value": 1.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared from 1-(3-amino-4-nitro-phenyl)-4-phenyl-1H-pyrrole-3-carbonitrile (Example E3) (254 mg, 0.835 mmol) and 3-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile (Example L1) ... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(3-amino-4-nitro-phenyl)-4-phenyl-1H-pyrrole-3-carbonitrile"}], "amount": {"mass": {"value": 254.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(2,2-dimethyl-6-... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of N-[5-(4-methyl-piperazin-1-yl)-2-trifluoromethoxy-phenyl]-acetamide (4.75 g, 15 mmol) in EtOH (100 mL) was treated with HCl 37% (35 mL). After 1 h under reflux the mixture was concentrated and... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-[5-(4-methyl-piperazin-1-yl)-2-trifluoromethoxy-phenyl]-acetamide"}], "amount": {"mass": {"value": 4.75, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was synthesized in analogy to Example 75, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, hydroxymethyl-cyclopropan, 4-(trifluoromethoxy)-phenylboronic acid and (1R,2R)-2-amino-cyclohex... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(1R,2R)-2-amino-cyclohexanol hydrochloride"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-bromo-6-chloro-3-pyridinecarboxylic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of ethyl 3-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]propionate (5.0 g, 16 mmol) in THF (120 ml) under N2 was added, dropwise, methylmagnesium bromide (15.6 ml of a 3.0M solution in ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NH4Cl"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 3-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]propionate"}], "a... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
0.58 g (0.00266 mol) of 4,6-dichloro-2-pyrrolidin-1-yl-pyrimidine and 1.36 g (0.00539 mol) of N-(4-sulfamoyl-phenyl) -acetamide potassium salt were stirred in 10 ml of 1-methyl-2-pyrrolidone at 140° C. for ... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4,6-dichloro-2-pyrrolidin-1-yl-pyrimidine"}], "amount": {"mass": {"value": 0.58, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-(4-sulfamoyl-phenyl) -acetamide potassium salt"}], "amount":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 3-(4-bromobutyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-one (6.80 g), 1-(1-phenyl-1H-indol-3-yl) piperazine dihydrochloride (4.80 g), diisopropylethyl amine (8.16 g), K2CO3 (9.50 g), NaI (400 m... | {"inputs": {"m1_m2_m3_m4_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(4-bromobutyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-one"}], "amount": {"mass": {"value": 6.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-(1-phenyl-1H-indol-3-yl) piperazin... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
60 g of 5-(2-fluorophenyl)-cyclohexane-1,3-dione were dissolved in 500 ml of concentrated sulfuric acid at -20° C. and nitrated with 18.3 g of 98% strength nitric acid at -20° C. in the course of 60 minutes... | {"inputs": {"m1_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(2-fluorophenyl)-cyclohexane-1,3-dione"}], "amount": {"mass": {"value": 60.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "nitric acid"}], "reaction_role": "REACTANT"}, {"identifiers": [... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
10% Palladium on carbon (0.574 g, 0.54 mmol) was added to 6-[4-[4-(benzyloxy)phenoxy]piperidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (2.53 g, 5.39 mmol) in MeOH (30 mL) under an atmosph... | {"inputs": {"m2_m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "6-[4-[4-(benzyloxy)phenoxy]piperidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine"}], "amount": {"mass": {"value": 2.53, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Palladiu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
7-Amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (3.96 g, 14 mmol) was reacted with trifluoroethylmercaptoacetyl chloride in the same manner as described in Example 1. After s... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "7-Amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid"}], "amount": {"mass": {"value": 3.96, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trifluoroethylmercaptoacety... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A crosslinked latex resin emulsion comprised of crosslinked resin or polymer particles derived from the emulsion polymerization of styrene, butyl acrylate, beta carboxyl ethyl acrylate (Beta CEA) and diviny... | {"inputs": {"m7": {"components": [{"identifiers": [{"type": "NAME", "value": "beta carboxyl ethyl acrylate"}], "amount": {"mass": {"value": 16.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m11": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"mass": {"value": 230.0, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
At room temperature, to a solution of 106a (153 mg 0.22 mmol) in THF/iPA/H2O (6 mL/6 mL/2 mL) was added LiOH (70 mg, 2.9 mmol) while stirring. This mixture was stirred for 0.5 h. Then, H2O (20 mL) was added... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "106a"}], "amount": {"mass": {"value": 153.0, "units": "MILLIGRAM"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 2-(4-(benzyloxy)tetrahydrofuran-2-yl)acetaldehyde (2.46 g, 11.17 mmol) in methanol (50 mL) was added NaBH4 (0.423 g, 11.17 mmol), in small portions, at room temperature. After 2 h, ... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(4-(benzyloxy)tetrahydrofuran-2-yl)acetaldehyde"}], "amount": {"mass": {"value": 2.46, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaBH4"}], "amount": {"mass": {"value": 0.423, "units":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-carbamic acid tert-butyl ester (1.59 g, 5.91 mmol) in 30 mL of dichloromethane and 15 mL of trifluoroacetic acid was stirred for 5 h then concentrated t... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(6-chloro-imidazo[1,2-b]pyridazin-8-yl)-carbamic acid tert-butyl ester"}], "amount": {"mass": {"value": 1.59, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"v... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of tert-butyl ((4S,6S)-4-(6-amino-3-fluoropyridin-2-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)carbamate (7k, 0.101 mg, 0.13 mmol) in EtOAc (4 mL) was added 5-cyano-2-pyri... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "SOLVENT"}]}, "m1_m5_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl ((4S,6S)-4-(6-amino-3-fluoropyridin-2-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
DIPEA (0.8 ml, 4.58 mmol) was added to a mixture of (R)-1-(2-methoxy-6-(trifluoromethyl)benzyl)-5-oxopyrrolidine-2-carboxylic acid (234 mg, 0.74 mmol) and 3-amino-N-cyclopropyl-2-hydroxy-4-phenylbutanamide ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "HATU"}], "amount": {"mass": {"value": 337.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m6_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM"}], "reaction_role": "SOLVENT"}, {"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 4-(2-tert-butoxycarbonyl-vinyl)-3,5-dimethyl-benzoic acid methyl ester (11.2 g, 38.6 mmol) in ethanol (50 mL) and THF (50 mL), Pd/C (1.0 g, 10% Pd) is added. The mixture is stirred for 16 h... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2-tert-butoxycarbonyl-vinyl)-3,5-dimethyl-benzoic acid methyl ester"}], "amount": {"mass": {"value": 11.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 5-bromopyrimidine (10 g, 0.063 mol) in a mixture of dry THF (150 mL) and hexane (50 mL) was cooled to −100° C. To this cooled solution was added n-BuLi (4 g, 21 mL, 0.062 mol) over a period of... | {"inputs": {"m1_m6_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-bromopyrimidine"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hexane"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_rol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 1-bromo-4-fluorobenzene (5.00 ml, 45.5 mmol), magnesium turnings (3.32 g, 137 mmol), and a few iodine crystals in 70 ml dry THF were vigorously stirred for 4 hours under the protection of nitro... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "iodine crystals"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"va... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Example 8a (90 mg, 0.19 mmol) was reacted with piperidine (8.0 eq.) as described under General Procedure G and the crude mixture was purified by flash chromatography (silica gel, DCM/MeOH 100:0, 49:1) to af... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Example 8a"}], "amount": {"mass": {"value": 90.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "piperidine"}], "reaction_role": "REACTANT"}]}}, "conditions": {"condit... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 3-(2-(N-t-butoxycarbonylamino)-ethoxy)-5-chloro-1,2-benzisoxazole (0.50 g) was added a solution of 4N-hydrochloric acid/1,4-dioxane (4.0 ml) and stirred at room temperature for 15 minutes. After filterin... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(2-(N-t-butoxycarbonylamino)-ethoxy)-5-chloro-1,2-benzisoxazole"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid 1,4-dioxane"}], "amount"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Intermediate 10 was coupled with the product of Example 27, step B following the procedure of Example 27, step C. The crude product was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl aceta... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 10"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 2-(3-pyridyl)-4-methylpyrimidine-5-carboxylic acid (215 mg, 1 mmol, prepared according to the general procedure described in Example 42, steps 1 and 2) and O-(7-azabenzotriazol-1-yl)-N,N,N,N-te... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Methylsulfamoylbenzylamine hydrochloride"}], "amount": {"mass": {"value": 355.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(3-pyridyl)-4-methylpyrimidine-5-ca... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Trifluoroacetic acid (2 mL) is added to a solution of [1-(4-trifluoromethyl-phenyl)-piperidin-4-yloxy]-acetic acid tert-butyl ester (769 mg; 2.14 mmol, prepared in accordance with Example 10) in dichloromet... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Trifluoroacetic acid"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "[1-(4-trifluoromethyl-phenyl)-piperidin-4-yloxy]-acetic acid tert-butyl este... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of (1aS,5aR)-1-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone (600 mg, 2.72 mmol) and terephthalaldehyde (913 mg, 6.81 mmol) in ethanol (10 mL) and approx. 6 N ... | {"inputs": {"m7": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m8_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "isopropanol"}], "amount": {"volume": {"value": 5.0, "units": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Triethylamine (370 μl, 2.65 mmol) was added slowly to a mixture of (R)-3-chloro-2-hydroxypropan-1-aminium 2,2,2-trifluoroacetate (210 mg, 0.88 mmol) in dichloromethane (2.0 mL) at 0° C. The mixture was stir... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Triethylamine"}], "amount": {"volume": {"value": 370.0, "un... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of the product from Step 9 (0.46 g, 1.1 mmol) and Amberlyst-15 (0.50 g) in xylene (10 mL) was heated at 140° C. for 2 h. The reaction mixture was filtered and the filtrate was concentrated. The re... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 0.46, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "15"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"iden... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Chloro-pyridin-3-ylamine (1.00 g, 7.75 mmol) in dichloromethane (20 mL) at 23° C. was treated with methane sulfonyl chloride (2.23 g, 19.4 mmol) and triethylamine (1.96 g, 19.4 mmol). After stirring for 4... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Chloro-pyridin-3-ylamine"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methane sulfonyl chloride"}], "amount": {"mass": {"value": 2.23, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A suspension of 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (Intermediate 31-4; 348 g, 1169 mmol) (80% strength by proton NMR), 6-chloro-3,5-dimethylpyrazine-2-carboxamide (217 g, 1169 mm... | {"inputs": {"m8": {"components": [{"identifiers": [{"type": "NAME", "value": "Dichloro[1,1\u2032-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct"}], "amount": {"mass": {"value": 8.6, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m2_m3_m4_m5_m6_m7": {"components": [{"identifiers": [{"type":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2.0 g of 3-[2-(5,5-dimethyl-[1,3]dioxan-2-yl)-4,5-dimethoxy-phenyl]-5-methyl-[1,2,4]-oxadiazole were stirred in 100 ml of acetone in the presence of 10 ml of concentrated HCl for 3 hrs. at room temperature.... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[2-(5,5-dimethyl-[1,3]dioxan-2-yl)-4,5-dimethoxy-phenyl]-5-methyl-[1,2,4]-oxadiazole"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
60% Sodium hydride (310 mg, 7.6 mmol) was washed with hexane (5.0 mL), and the residue was suspended in N,N-dimethylformamide (20 mL). 2-tert-Butoxycarbonylamino-4-(tert-butyldimethylsilyloxymethyl)pyridine... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "amount": {"volume": {"value": 70.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 20.0, "units": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 6-chloro-nicotinonitrile (2.1 g, 15.16 mmol, 1.0 equiv; commercially available) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (4.86 g, 24.25 mmol, 1.6 equiv; commercially available)... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2CO3"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 10 g (0. 037 mole) of 3,5-dimethoxy-4-hydroxy-2,β-dinitrostyrene and 10 g of palladium hydroxide on charcoal in 400 cm3 of ethanol and 7 cm3 of formic acid is heated under reflux for 3 hours. A... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3,5-dimethoxy-4-hydroxy-2,\u03b2-dinitrostyrene"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 400.0, "un... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Duloxetine is acid labile, and acid hydrolysis of its ether linkage results in a thienyl alcohol and 1-naphthol. 50% of a dosage is hydrolyzed to 1-naphthol within one hour at a pH of 1.0, which is achieved... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Duloxetine"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifie... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a cooled (0° C.) solution of 11a (500 mg, 2.7 mmol) in DMF (30 ml), NaH (130 mg, 3.2 mmol) was added. The mixture was stirred for 10 min. and a solution of p-toluensulphonyl chloride (570 mg, 3.0 mmol) i... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "p-toluensulphonyl chloride"}], "amount": {"mass": {"value": 570.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "rea... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Using a method analogous to that described in Example 40, 4-bromophenyl-sulfonic acid-(5-hydroxypentyl)-amide and 4-hydroxyphenyl boronic acid were reacted to give the title compound as a white solid. δC (D... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-bromophenyl-sulfonic acid-(5-hydroxypentyl)-amide"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-hydroxyphenyl boronic acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"condit... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 7-bromo-1-tetralone (11.25 g), pyridin-3-carboxaldehyde (5.35 g), acetic acid (5 ml) and piperidine (6 ml) was heated on a steam bath for 6 hours and then allowed to stand for 18 hours. The vol... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "7-bromo-1-tetralone"}], "amount": {"mass": {"value": 11.25, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridin-3-carboxaldehyde"}], "amount": {"mass": {"value": 5.35, "units": "GRAM"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4-Chloroaniline (52.7 kg, 413 mol) was dissolved in a mixture of t-butyl methyl ether (180 kg), 30% aqueous sodium hydroxide (61.6 kg, 463 mol) and water (24.2 kg), then cooled to 15° C. To the resulting sl... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "trimethylacetyl chloride"}], "amount": {"mass": {"value": 52.2, "units": "KILOGRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Chloroaniline"}], "amount": {"mass": {"value":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
5-Chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)-6-nitrobenzimidazole (1.2 g) was dissolved in 2.5N hydrochloric acid (20 ml) and thereto was added zinc powder (1.5 g) in portions and the mixture was stirred... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "zinc"}], "amount": {"mass": {"value": 1.5, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-Chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)-6-nitrobenzimidazole"}], "amoun... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4-Butoxy-(2,3-difluorophenyl)cyclohexene (48) (11.0 g) and THF (200 ml) were put in a reaction vessel under a nitrogen atmosphere, and cooled to −74° C. sec-Butyllithium (1.00 M, in a n-hexane and cyclohexa... | {"inputs": {"m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ice water"}], "amount": {"volume": {"value": 500.0, "units": "MILLILITER"}}, "reaction_role": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In analogy to the procedure described for the synthesis of example 2 (step b), the title compound rac-[(3R,4S)-1-(1-cyclopropylmethyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-c... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-methoxy-phenyl chloroformate"}], "reaction_role": "REACTANT"}]}, "m0_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "rac-(1-cyclopropylmethyl-piperidin-4-yl)-[(3S,4R)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-m... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of dodecyl 4-(4-nitrophenyl)-4-oxobutyrate (0.42 g, 1.1 mmol), in ethyl acetate (50 ml) and 10% palladium on carbon (0.10 g) were shaken under hydrogen (30-40 psi) for 10 minutes. The mixture was... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "dodecyl 4-(4-nitrophenyl)-4-oxobutyrate"}], "amount": {"mass": {"value": 0.42, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 50.0, "units": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Under N2 atmosphere, the Boc-DPro-3-piperidinamide was dissolved in ml of CH2Cl2 and 10 ml of trifluoracetic acid added while stirring. The reaction mixture was stirred for 30 min. All volatiles were remove... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Boc-DPro 3-piperidinamide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "trifluoracetic acid"}], "amount": {"volume": {"v... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Methyl 2-methoxyimino-2-(3-chloro-4-methoxyphenyl)acetate (syn isomer) (2.7 g.) and a 2N aqueous solution of sodium hydroxide (10.6 ml.) were treated according to a similar manner to that of Preparation 5-(... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Methyl 2-methoxyimino-2-(3-chloro-4-methoxyphenyl)acetate"}], "amount": {"mass": {"value": 2.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "aqueous solution"}], "reaction_role": "REACTANT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Add methyl iodide (20 mg, 0.164 mmol) at r.t. to a mixture of 3-phenylsulfanyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid methylamide (Ia-33, 47 mg, 0.166 mmol), Cs2CO3 (65 mg, 0.2 mmol) and pyridine (1.5 ... | {"inputs": {"m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3-phenylsulfanyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid methylamide"}], "amount": {"mass": {"value": 47.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Cs2CO3"}], "amount": {"mas... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2H-1,4-benzothiazin-3(4H)-one (1.65 g, 10 mmol) and indole-3-carboxaldehyde (1.45 g, 10 mmol) in piperidine (30 ml) was heated under reflux for 5 days. The solvent was removed in vacuo, ethano... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2H-1,4-benzothiazin-3(4H)-one"}], "amount": {"mass": {"value": 1.65, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "indole-3-carboxaldehyde"}], "amount": {"mass": {"value": 1.45, "units": "G... |
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