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:
A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (360 mg, 1 mmol), imidazolidin-2-one (430 mg, 5 mmol), copper(I) iodide (115 mg, 0.6 mmol), N,N-dimethylglycine hy... | {"inputs": {"m1_m2_m6_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid"}], "amount": {"mass": {"value": 360.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "imidazolid... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared as in Example 24a from 4-(2-cyano-3-nitrophenoxy)cyclohexanecarboxylic acid (Example 154d) and methylamine hydrochloride as an orange solid (80%). MS 304 (MH+).
### ORD JSON:
| {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2-cyano-3-nitrophenoxy)cyclohexanecarboxylic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methylamine hydrochloride"}], "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:
Oleic acid (5 g, 17.7 mmol) were dissolved in 20 ml dry acetonitrile and the mixture was refluxed for 24 hours. The solvent was removed under reduced pressure.
### ORD JSON:
| {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Oleic acid"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
11.3 gm (38.5 millimols) of N-(p-amino-phenethyl)-N'(m-tolyl)-piperazine, 4.6 gm (38.5 millimols) of 3-chloropropyl-isocyanate and 120 ml of toluene were admixed with each other, accompanied by gentle agita... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(p-amino-phenethyl)-N'(m-tolyl)-piperazine"}], "amount": {"mass": {"value": 11.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-chloropropyl-isocyanate"}], "amount": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared from tert-butyl (2R,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate (i-4b) and (2-amino-1,3-thiazol-4-yl)acetic acid acc... | {"inputs": {"m0_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl (2R,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(2-amino-1,3-thiazol-4-yl)acetic acid"}],... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a mixture of 2-amino-3',4,4',5-tetramethoxybenzophenone (6.6 g), ethyl 4-chloroacetoacetate (3.7 g) and acetic acid (60 ml) was added concentrated sulfuric acid (0.3 ml) and the mixture was stirred at 10... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-3',4,4',5-tetramethoxybenzophenone"}], "amount": {"mass": {"value": 6.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl 4-chloroacetoacetate"}], "amount": {"mass": {"value": 3.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 100 ml flask was loaded with 6-bromo-methyl-benzooxazole (1.8 g, 8.5 mmole), 40 ml DMF and sodium azide (1.1 g, 16.98 mmole). The reaction mixture was stirred at room temperature, overnight. The reaction ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "pure product"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "6-bromo-methyl-benzooxazole"}], "amount": {"mass": {"value": 1.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"iden... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(2S,5R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 133, 2.194 g, 5.29 mmol) in DCM (65 mL) was cooled in an ice-bat... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Dess-Martin periodinane"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 26.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2_m4": {"components": [{"identi... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(1S,2R,3S,4R)-3-Amino-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester (prepared as described in Example 6k, 0.5 g, 2.7 mmol) was dissolved in methanol (25 mL). Isovaleraldehyde (0.233 g, 2.7 mmol) was a... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium cyanoborohydride"}], "amount": {"mass": {"value": 0.424, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 1.0, "units": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
0.15 ml of a 1N aqueous solution of lithium hydroxide was added to a solution of 30 mg (0.13 mmol) of ethyl 4-(N,N-dimethylamino)phenoxyacetate (prepared as described in Preparation 18) in 1 ml of methanol,... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "aqueous solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium hydroxide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl 4-(N,N-dimethylamino)phenoxyacetate"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of (2S,4R)-4-(t-butyldimethylsilyloxy)-2-(2-chloropropionyl)aminomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (18.4 g), potassium cyanate (14.9 g) and tetrabutylammonium iodide (13.6 g) in N,N-... | {"inputs": {"m1_m2_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "(2S,4R)-4-(t-butyldimethylsilyloxy)-2-(2-chloropropionyl)aminomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine"}], "amount": {"mass": {"value": 18.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "v... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
NaOH (160 mg, 4.0 mmol) was added to a stirred solution of ethyl {[7-anilino-5-oxo-8-phenyl-4-(trifluoromethyl)-5,8-dihydro-1,8-naphthyridin-2-yl]sulfanyl }acetate (30.0 mg, 0.060 mmol) in aqueous EtOH (10 ... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount": {"mass": {"value": 160.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl {[7-anilino-5-oxo-8-phenyl-4-(trifluoromethyl)-5,8-dihydro-1,8-naphthyridin-2-yl]sulfan... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Sodium hydride (60% dispersion in oil, 5 mg) was added at room temperature under an atmosphere of nitrogen to a solution of N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1H-pyrazol-5-yl]-2-phenyl-1-ethanesulfonamid... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "amount": {"volume": {"value": 4.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium hydride"}], "amount": {"mass": {"value": 5.0, "u... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
5-(3-Bromo-propoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.244 g, 0.605 mmol, 1 eq) was suspended in dry acetonitrile (10 mL) under Ar. Pyrrolidine (0.100 mL, 1.210 mmol, 2 eq) was added. The ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(3-Bromo-propoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester"}], "amount": {"mass": {"value": 0.244, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Pyrrolidine"}],... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(1-{2-[5-(7-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-dibenzothiophen-3-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (0.... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(1-{2-[5-(7-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-dibenzothiophen-3-yl)-1H-imid... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(3S,5R)-5-Methyl-3-[1-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-methanoyl]-heptanoic acid tert-butyl ester (7.26 g, 0.018 mol) in H2O (53 mL) and THF (176 mL) at 0° C. was added a premixed solution ... | {"inputs": {"m6_m7_m10": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bisulfite"}], "amount": {"mass": {"value": 7.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium sulfite"}], "amount": {"mass": {"value": 13.0, "units": "GRAM"}}, "reaction_role... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared in 95% yield from (5-bromo-2-fluorophenyl)acetaldehyde (0.98 g), 2-methyl-5-(1-piperazinyl)quinoline (0.51 g) and sodium triacetoxyborohydride (0.95 g) according to the proce... | {"inputs": {"m0_m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(5-bromo-2-fluorophenyl)acetaldehyde"}], "amount": {"mass": {"value": 0.98, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-methyl-5-(1-piperazinyl)quinoline"}], "amount": {"mass": {"val... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Tert-Butyl-[5″-(3-methoxy-phenyl)-[2,2′;4′,3″]terpyridin-6′-yl]-amine (1 eq, 0.073 mmol, 0.030 g) is dissolved in TFA (6 ml)/DCM (1 ml) and the reaction mixture is heated at 70° C. for 5 hours. The reaction... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Tert-Butyl-[5\u2033-(3-methoxy-phenyl)-[2,2\u2032;4\u2032,3\u2033]terpyridin-6\u2032-yl]-amine"}], "amount": {"mass": {"value": 0.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of NH4Cl (13.5 9, 251 mmol) in 170 mL toluene at 0° C. was added a 2.0 M solution of AlMe3 (126 mL, 251 mmol) dropwise. The mixture was warmed to room temperature and stirred for 4 hours. 2-... | {"inputs": {"m8": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Allyl-2-(3-methoxy-phenyl)-pent-4-enenitrile"}], "amount": {"m... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a vial charged with 1-(5-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide (0.100 g, 0.210 mmol) and Pd(Ph3P)4 (0.024 g, 0.021 mmol) in THF (1.050 ml) was added pyridin-2-... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "pyridin-2-ylzinc(II) bromide"}], "amount": {"volume": {"value": 2.1, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(5-bromo-2-methoxyphenyl)-N-(isoxazol-3-yl... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1.18 g (7.9 mmol) of p-dimethylaminobenzaldehyde are added to a solution of 2.7 g (7.9 mmol) of 1-amino-2-ethyl-3-(p-methoxyphenacyl)-2-ethylimidazolium bromide in 40 ml of glacial acetic acid. The mixture ... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "p-dimethylaminobenzaldehyde"}], "amount": {"mass": {"value": 1.18, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-amino-2-ethyl-3-(p-methoxyphenacyl)-2-ethylimidazolium bromide"}], "amount... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 3-[4-benzyloxy-3-(tert-butoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester (8.50 g, 21.3 mmol) in THF (100 mL) was treated with 5% Pd-on-carbon (1.1 g) and shaken under a hydrogen ... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[4-benzyloxy-3-(tert-butoxycarbonylamino-methyl)-phenyl]-propionic acid methyl ester"}], "amount": {"mass": {"value": 8.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd on-carbon"}], "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In the presence of 0.6 g of paratoluenesulfonic acid, 50 g (0.4 mol) of cyclooctanone and 100 ml (0.9 mol) of isopropenyl acetate were refluxed for 11 hours. The reaction mixture was cooled, stirred with 0.... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "amount": {"mass": {"value": 0.6, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "paratoluenesulfonic acid"}], "amount": {"mass": {"value": 0.6, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a preferred method of preparing F-Dopa, 2-fluoro-4,5-dimethoxybenzaldehyde is reacted with tert-Butoxycarbonylamino-(dimethoxy-phosphoryl)-acetic acid ethyl ester to produce 2-tert-butoxycarbonylamino-3-... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "F-Dopa"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-fluoro-4,5-dimethoxybenzaldehyde"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-Butoxycarbon... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 2 ml of ethanol was suspended 0.3 g of 6-methylthio-4-benzoylpyrimidine, to which 0.07 g of sodium borohydride was added, followed by stirring at 0° C. for 4 hours. The reaction mixture was then poured i... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "6-methylthio-4-benzoylpyrimidine"}], "amount": {"mass": {"value": 0.3, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Ester 1-3 (1.3 g, 6.5 mmol) was dissolved in 32 mL 6 N HCl. After stirring overnight, the resulting suspension was concentrated, providing acid 1-4 as a white solid.
### ORD JSON:
| {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Ester"}], "amount": {"mass": {"value": 1.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 32.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1-Chloro-N,N,2-trimethylprop-1-en-1-amine (Ghosez's reagent, 7.85 mL, 59.3 mmol) was added drop-wise to a solution of C5 (9.30 g, 19.8 mmol) in dichloromethane (200 mL). After 1 hour at room temperature, th... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-Chloro-N,N,2-trimethylprop-1-en-1-amine"}], "amount": {"volume": {"value": 7.85, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "C5"}], "amount": {"mass": {"value": 9.3, "units": "GRA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A suspension of (R)-N-(1-(2-(tert-butyldiphenylsilyloxy)ethyl)-1H-pyrazol-5-yl)-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo pyrimidine-3-carboxamide (201 mg, 0.285 mmol) in 4M HCl in dioxa... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-N-(1-(2-(tert-butyldiphenylsilyloxy)ethyl)-1H-pyrazol-5-yl)-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo pyrimidine-3-carboxamide"}], "amount": {"mass": {"value": 201.0, "units": "MILLIGRAM"}}, "reaction_role": "REA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
N2-{4-[4-(bromoacetyl)phenyl]isothiazol-3-yl}-N1-(cyanomethyl)leucinamide (29 mg, 0.064 mmol) was dissolved in DMF (0.6 mL) and dimethylamine (0.13 mL of a 2 M solution in THF, 0.26 mmol) was added. The rea... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "reaction_role": "REACTANT"}]}, "m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethylamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REAC... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
312 mg (purity 91%, 1.11 mmol) of 4-(5-chloro-2-cyanophenyl)-6-oxo-1,6-dihydropyridin-3-carbonitrile and 1.5 eq. of 2-bromopropanoic acid (racemate) were reacted according to General Method 4A at 45° C. Yie... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(5-chloro-2-cyanophenyl)-6-oxo-1,6-dihydropyridin-3-carbonitrile"}], "amount": {"mass": {"value": 312.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-bromopropanoic acid"}], "reactio... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-Methoxypyridine-2-amine (780 mg) was added to a toluene (50 mL) solution of 3-(chlorosulfonyl)benzoyl chloride (3.00 g), and stirred overnight at room temperature. Ethyl acetate was added to the reaction ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl acetate"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Methoxypyridine-2-amine"}], "amount": {"mass": {"value": 780.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 5-(chloromethyl)oxazolidin-2-one (45 μmol) was added the solution of 3-(4-(methylamino)-2-(pyridin-3-yl)quinazolin-6-yl)phenol (30 μmol) in NMP (200 μL). PS-BEMP (90 μmol) was added to the vials by resin... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(chloromethyl)oxazolidin-2-one"}], "amount": {"moles": {"value": 45.0, "units": "MICROMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-(4-(methylamino)-2-(pyridin-3-yl)quinazolin-6-yl)phenol"}], "am... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 10.2 g of 17β-acetoxy-7α-(5-acetoxypentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene in 205 ml of methanol is stirred with 33.7 ml of sodium hydroxide solution for 45 minutes at 15° C... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "reaction_role": "SOLVENT"}]}, "m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "17\u03b2-acetoxy-7\u03b1-(5-acetoxypentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene"}], "amount": {"mass": {"va... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
N-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy-5-iodobenzamide (950 mg, 2 mmol) and trimethylsilylacetylene (246 mg, 2.5 mmol) were dissolved in triethylamine (2 mL) and N,N-dimethylformamide (4 mL). Tetrakis... | {"inputs": {"m8_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "cuprous iodide"}], "amount": {"mass": {"value": 4.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Tetrakis(triphenylphosphine)palladium"}], "amount": {"mass": {"value": 23.0, "units": "M... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Benzyl 4-(8-methylimidazo[1,5-a]pyrazin-3-yl)piperidine-1-carboxylate (3.71 mmol, 1.30 g) was dissolved in 37% hydrochloric acid (240 mmol, 20 ml). The reaction mixture was stirred at room temperature for t... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Benzyl 4-(8-methylimidazo[1,5-a]pyrazin-3-yl)piperidine-1-carboxylate"}], "amount": {"mass": {"value": 1.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volu... |
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-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]hydroxyamine (700 mg, 1.93 mmol) in THF (10 ml) containing triethylamine (1.2 eq.) is added chloromethylacetate (2 eq.). The ... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-methyl-N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]hydroxyamine"}], "amount": {"mass": {"value": 700.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "re... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of 10.1 g (33 mmole) of cis-1-(2,4-dimethoxybenzyl)-3-azido-4-oxo-azetidine-2-carboxylic acid (prepared by reacting the product of example 1 with potassium carbonate in aqueous tetrahydrofur... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "cis-1-(2,4-dimethoxybenzyl)-3-azido-4-oxo-azetidine-2-carboxylic acid"}], "amount": {"mass": {"value": 10.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "pyridine"}], "am... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (100 mg, 0.238 mmol) was placed in a 50 ml round bottom flask and dissolved in DMF (3 ml); EDC (45.6 ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-h... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a microwave tube was added 1 eq. of ethyl 2,4-dichloropyrimidine-5-carboxylate (200 mg, 0.91 mmol), 0.5 eq. of 3-chlorophenyl boronic acid (67 mg), 0.1 eq. of Pd2(dba)3 (83 mg), 3 eq. of K3PO4 in 4 mL of... | {"inputs": {"m1_m2_m6_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2,4-dichloropyrimidine-5-carboxylate"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-chlorophenyl boronic acid"}], "amount": {"mass"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared from 0.500 g of 6-amino-4-(3-bromophenylamino)quinoline-3-carbonitrile, 0.194 g of Et3N and 0.202 g of methacryloyl chloride in the same manner as EXAMPLE 380. There was obtained 0.317 g of N-[4-(3... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "6-amino-4-(3-bromophenylamino)quinoline-3-carbonitrile"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methacryloyl chloride"}], "amount": {"mass": {"val... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 3,3-dimethylbutyraldehyde (13 mg, 0.13 mmol) and the spiro-piperidine (B5) (25 mg, 0.10 mmol) in dry dichloromethane (2 ml) was stirred at room temperature for 30 min, cooled with ice-bath, an... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3,3-dimethylbutyraldehyde"}], "amount": {"mass": {"value": 13.0,... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared from (RS)-[4-chloro-2-(3-oxo-3-{3-[5-(tetrahydro-pyran-2-yloxymethyl)-[1,2,3]triazol-1-yl]-phenyl}-propionylamino)-5-piperidin-1-yl-phenyl]-carbamic acid tert.-butyl ester (E... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(RS)-[4-chloro-2-(3-oxo-3-{3-[5-(tetrahydro-pyran-2-yloxymethyl)-[1,2,3]triazol-1-yl]-phenyl}-propionylamino)-5-piperidin-1-yl-phenyl]... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
0.32 ml of ethyl 2(R)-trifluoromethanesulphonyloxypropionic acid and 0.075 g of sodium hydride dispersion (55%) are added at −45° C. to the solution of 0.733 g of tert-butyl 3-hydroxy-4-{4-[3-(2-methoxybenz... | {"inputs": {"m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2(R)-trifluoromethanesulphonyloxypropionic acid"}], "amount": {"volume": {"value": 0.32, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 2-azido-1-phenylvinyl 3-cyclopentylpropionate from Step A (4.0 g, 14 mmol) in dry cyclohexane (10 mL) was added triethyl phosphite (12 g, 74 mmol) dropwise. After stirring at room t... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-azido-1-phenylvinyl 3-cyclopentylpropionate"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethyl phosphite"}], "amount": {"mass": {"value": 12.0, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine (200 mg), methyl 1,2,3,4-tetrahydroquinoline-6-carboxylate (323 mg), tris(dibenzylideneacetone)dipalladium(0) (19 mg), (R)-(+)... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m5_m3_m4_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine"}], "amount": {"mass": {"value": 200.0, "units": "MIL... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 4-iodoaniline (1 g, 4.5 mmol), 2-fluorobenzaldehyde (0.48 ml, 0.566 g, 4.5 mmol) and triacetoxyborohydride (1.9 g, 9.0 mmol) in 1,2-dichloroethane (20 ml) was stirred for 4 days at room temper... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-iodoaniline"}], "amount": {"mass": {"value": 1.0, "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:
To a stirred mixture of 6-tert-butoxycarbonylnicotinic acid (1.9 g, 8.51 mmol) and triethylamine (1.17 g, 11.49 mmol) in tert-BuOH (30 ml) and toluene (30 ml) was added a solution of diphenyl phosphoryl azi... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "6-tert-butoxycarbonylnicotinic acid"}], "amount": {"mass": {"value... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound is prepared from 2-amino-N-(1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)oxazole-5-carboxamide (30 mg, 0.08 mmol, Step-1, single enantiomer) and cyclopropanecarbonyl chloride (... | {"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-N-(1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)oxazole-5-carboxamide"}], "amount": {"mass": {"value": 30.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "cyclopropa... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-(N-Allyl-N-n-propylamino)-5-trifluoromethane-sulfonyloxychroman (0.28 g, 0.74 mmol), LiCl (0.097 g, 2.3 mmol), PdCl2 (dppf) (0.031 g, 0.04 mmol) and 2.6-di-t-butyl-4-methylphenol (0.005 g) were dissolved ... | {"inputs": {"m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Tetramethyltin"}], "amount": {"volume": {"value": 0.12, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m6_m7_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(N-Allyl-N-n-propylamino)-5-trifluoromethane-sulf... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
18 g (0.2 mol) of methyl hydroxyacetate and 20.2 g (0.2 mol) of triethylamine are first introduced into 300 ml of dichloromethane at 0° C. 41.9 g (0.22 mol) of toluenesulfonyl chloride are then added at thi... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Ice water"}], "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl hydroxyacetate"}], "amount": {"mass": {"value": 18.0, "units": "GRAM"}}, "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 3-(2,4-dimethoxybenzyl)-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (2 g), 4′-(hydroxymethyl)-3′-methoxybiphenyl-2-carbonitrile (1.7 g), 1,1′-(azodicarbonyl)dipiperidine (2.2 g), tributylph... | {"inputs": {"m1_m2_m3_m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(2,4-dimethoxybenzyl)-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4\u2032-(hydroxymethyl)-3\u... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1.00 g of 1-(diphenylmethyl)piperazine was dissolved in 10 ml of N,N-dimethylformamide; 0.42 ml of 2-(2-chloroethoxy)ethanol, 0.59 g of sodium iodide and 0.66 g of potassium carbonate were added, followed b... | {"inputs": {"m1_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(diphenylmethyl)piperazine"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 10.0, "units": "MILLIL... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
N(3(S)) 2[1,2-Dihydro-6-methyl-2-oxo-3-(3-phenylpropionyl)amino-1-pyridyl]-N-(2-benzyloxy-5-oxotetrahydrofuran-3-yl)acetamide (53e), was obtained (67%) as a mixture of anomers: IR (KBr) 3282, 1774, 1667, 16... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2[1,2-Dihydro-6-methyl-2-oxo-3-(3-phenylpropionyl)amino-1-pyridyl]-N-(2-benzyloxy-5-oxotetrahydrofuran-3-yl)acetamide"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "KBr"}], "reaction_role... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Trifluoroacetic acid (5 mL) was added to a dichloromethane (5 mL) solution of the obtained tert-butyl 4-(5-{(1R)-1-[4-(cyclobutylcarbonyl)phenoxy]propyl}-1,2,4-oxadiazol-3-yl)-2-fluorobenzoate at room tempe... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Trifluoroacetic acid"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert-butyl 4-(5-{(1R)-1-[4-(cyclobutylcarbonyl)phenoxy]propyl}-1,2,4-oxadiaz... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of compound 75 (200 mg, 0.79 mmol) in methanol (10 mL) was added to Raney Nickel (slurry in H2O, 50 mg) in a round bottom flask. The suspension was heated at reflux for 10 minutes then filtered t... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "compound 75"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_r... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 13.3 g portion of 3-chloro-7-[3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine and 7 g of sodium cyanoborohydride in 150 ml of acetic acid, were reacted as described in Example 1, giving 6.7 g of 3-chl... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-chloro-7-[3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium cyanoborohydride"}], "amount": {"mass": {"value": 7.0, "units": "GRAM"}}, "reaction_rol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound is prepared in 44% yield (10 mg) from 2-amino-5-chloro-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamide (20 mg, 0.053 mmol, single enantiomer, Step-1) and propionyl chlor... | {"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-5-chloro-N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)isonicotinamide"}], "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "propionyl chlori... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The synthesis of this compound is carried out as described in Example 1, except that in Step B(1) an equivalent amount of 1,1,1-trifluoro-5-bromopentane is substituted for amyl bromide. The product of Step ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1,1,1-trifluoro-5-bromopentane"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1-chloro-9,9,9-trifluoro-4-nonanol"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(piperazin-1-yl)-1,3,5-triazin-2-yl)phenyl)-3-(pyridin-4-yl)urea-2TFA (115 mg) in 1:1 98% formic acid and 37% formalin (4 mL) was heated at 75° C. for 90 minu... | {"inputs": {"m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(piperazin-1-yl)-1,3,5-triazin-2-yl)phenyl)-3-(pyridin-4-yl)urea-2TFA"}], "amount": {"mass": {"value": 115.0, "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:
The title compound was prepared by a procedure similar to the one described for 3-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-6-oxopyrimidin-1(6H)-yl]-4-methyl-N-{1-[(methylamino)carbonyl]methyl}benzamide using et... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N-methylmorpholine"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-6-oxopyrimidin-1(6H)-yl]-4-methyl-N-{1-[(methylamino)carbonyl]methyl}benzamide"}],... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of n-butylithium in hexane (13.2 mL of 1.6 M, 21 mmol) is added to a stirred solution of 5-bromo-indane (1.06 g 4 mmol) in dry tetrahydrofuran (30 mL) at −75° C. under an argon atmosphere. The mi... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane"}], "amount": {"volume": {"value": 13.2, "units... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Benzenesulfonyl chloride (0.45 ml in 10 ml dichloromethane, 3.5 mmol) was added dropwise to a stirring solution of 1-(4-aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinoline-4-amine (1.0 g, 3.2 mmol), dichlorometh... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Benzenesulfonyl chloride"}], "amount": {"volume": {"value": 0.45, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-(4-aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinoline-4-amine"}], "amo... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of methyl 4-chloro-1-(3-hydroxypropyl)-2-[(6-methoxy-2-methylpyridin-3-yl)amino]-1H-benzimidazole-7-carboxylate (Reference example 156, 6.40 g, 15.81 mmol) in tetrahydrofuran (42.0 mL) were ad... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 4.27, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m5_m2_m3": {"componen... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The coupling of (4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (XI-1) and 5-(but-2-ynyloxy)pyrazine-2-carboxylic acid [G. Csjernyik et al. WO2012087237 (20... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(but-2-ynyloxy)pyrazine-2-carboxylic aci... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of Compound 19 (5 g, 12.24 mmol) in 30 mL neat phosphorus oxychloride was heated at 100° C. for 3 h. The solvent was evaporated under reduced pressure. The residue was suspended in ice water and ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Compound 19"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "phosphorus oxychloride"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reacti... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of the alcohol from above (200 mg, 0.796 mmol) in CH2Cl2 (8 mL) was added activated MnO2 (814 mg, 7.96 mmol) and the mixture stirred at room temperature for 69 h. The reaction mixture was filt... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "alcohol"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "MnO2"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of Z-Ala-Val-Asp(OtBu)-Thr(tBu)-Ser(tBu)-Ser(tBu)-Glu(OtBu)-OC6H5 (20.16 g; 16.8 mmol) in DMF (400 mL) was hydrogenated with 5% Pd-BaSO4 (10 g) for 2 h in a Vibromixer apparatus. The reaction mix... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Z-Ala-Val-Asp(OtBu)-Thr(tBu)-Ser(tBu)-Ser(tBu)-Glu(OtBu)-OC6H5"}], "amount": {"mass": {"value": 20.16, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 4... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a mixture of methyl-m-toluate (180 g, 1.2 mol) and N-bromosuccimide (235 g, 1.32 mol) in CCl4 (2 L) was added in portion benzoyl peroxide (18 g, 0.1 times) at 50° C. The mixture was refluxed for 5 h. The... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "benzoyl peroxide"}], "amount": {"mass": {"value": 18.0, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl-m-toluate"}], "amount": {"mass": {"value": 180.0, "units... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
60 g (0.33 mol) of N-formyl-2-methyl-4-nitroaniline were dissolved in 500 ml of dimethylformamide. 184 g (1.33 mol) of potassium carbonate were added, and the resultant solution was warmed to 50° C. 152.8 g... | {"inputs": {"m5": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"mass": {"value": 350.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant solution"}], "reaction_role": "REACTANT"}]}, "m4": {"compo... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4-(6-hydroxy-indan-1-ylmethyl)-1H-imidazol-1-ium chloride (100 mg, 0.399 mmol) and 2,2-dimethylpropionic acid chloride (510 mmol) were reacted in TFA (1 ml) and purified as described in example 1. Yield 74 ... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(6-hydroxy-indan-1-ylmethyl)-1H-imidazol-1-ium chloride"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2,2-dimethylpropionic acid chloride"}], ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-vinylbenzamide (750 mg, 1.99 mmol) was dissolved in a solution of MeOH (14 mL) and DCM (28 mL). The resulting mixture was cooled to −78° C., O3 was... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-vinylbenzamide"}], "amount": {"mass": {"value": 750.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "amount": {"vol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
12-methoxy-11,13-dioxa-12-bora-dispiro[4.0.4.3]tridecane was prepared as follows. 5 g of bicyclopentyl-1,1′-diol was dissolved in 50 ml of trimethyl borate. The reaction mixture was stirred at room temperat... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "bicyclopentyl-1,1\u2032-diol"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trimethyl borate"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"... |
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 Example 68/69, step 8, using (1R,2R,4R)-2-(3,3-Difluoro-azetidine-1-carbonyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester and 4-Bromo-2-trifluo... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(1R,2R,4R)-2-(3,3-Difluoro-azetidine-1-carbonyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Bromo-2-trifluoromethyl-benz... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Following the procedure as described in Example 10, making variations as required to replace N-(4-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide with N-(4-(4-phenyl-4,5-dihydro-1H-imidazol-2-... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4-(4-phenyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide"}], "r... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The solid 2-[(6-chloropyridin-3-yl)methyl]-2-methylmalonic acid (8.70 g, 37.5 mmol) in a 500 mL round bottom flask was immersed in an oil bath heated to 185° C. As the solid melted carbon dioxide evolution ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[(6-chloropyridin-3-yl)methyl]-2-methylmalonic acid"}], "amount": {"mass": {"value": 8.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "carbon dioxide"}], "reaction_role... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 5.84 g (22 mmol) 1-(2-chloro-pyridin-4-yl)-4-cyclopentyl-piperazine, 0.8 g copper powder in 41 ml 7M ammonia in methanol was heated to 150° C. for 18 h. After evaporation to dryness the residue... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(2-chloro-pyridin-4-yl)-4-cyclopentyl-piperazine"}], "amount": {"mass": {"value": 5.84, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ammonia"}], "amount": {"volume": {"value": 41.0, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of (R)-2-methylpyrrolidine hydrochloride (4 g, 0.03 mol), 2-bromoethanol (3.7 g, 0.029 mmol) and K2CO3 (8.28 g, 0.0618 mol) in acetonitrile (50 mL) was stirred at room temperature overnight. The m... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-2-methylpyrrolidine hydrochloride"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-bromoethanol"}], "amount": {"mass": {"value": 3.7, "units": "G... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2-(4-bromobenzyloxy)-5-chloropyridine (Preparation 107, 0.12 g, 0.40 mmol), methanesulfonamide (0.10 g, 0.12 mmol), tri-tert-butylphosphonium tetrafluoroborate (12 mg, 0.04 mmol), Herrmann's p... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1,8-diazabicyclo[5.4.0]undec-7-ene"}], "amount": {"volume": {"value": 0.18, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3_m6_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(4-bromobenzyloxy)-5-chloropy... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared in an analogous manner to Example 129 starting from ethyl 2-(4-aminopiperidin-1-yl)-4-[(2-methoxyethoxy)methyl]-1,3-thiazole-5-carboxylate hydrochloride (Intermediate 126) and 3,4-dichloro-5-methyl... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "LiOH THF"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2-(4-aminopiperidin-1-yl)-4-[(2-methoxyethoxy)methyl]-1,3-thiazole-5-carboxylate hydrochloride"}], "reaction_role": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Gaseous ammonia (from a lecture bottle) was condensed into a suspension of 4-chloro-5-iodo-7-phenyl-7H-pyrrolo[2,3-d]pyrimidine (30 mg, 0.084 mmol) in dioxane (2 mL) and iPrOH (2 mL) in a sealable glass tub... | {"inputs": {"m2_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-5-iodo-7-phenyl-7H-pyrrolo[2,3-d]pyrimidine"}], "amount": {"mass": {"value": 30.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dioxane"}], "amount": {"volume": {"value": 2.0... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of butyllithium in hexanes (2.5 M; 15.9 ml) was added to a stirring solution of 3-fluoroanisole (5.0 g) in dry tetrahydrofuran (100 ml) at -78° C. and the mixture stirred at that temperature for ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "butyllithium"}], "reaction_role": "REACTANT"}, {"identifiers":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Ethyl 4-nitro-2-ethoxycinnamate obtained in step (i) was hydrogenated using Pd (10%)/C—H2 (60 psi) (11 g) in ethyl acetate (150 ml) at RT and chromatographed using ethyl acetate/hexane to yield the title co... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Pd"}], "reaction_role": "CATALYST"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl 4-nitro-2-ethoxycinnamate"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "C\u... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The product from Example 2g (275 mg, 1.33 mmol) was reacted with the product from Example 52b (307 mg, 1.33 mmol) for 18 h following the procedure from Example 1g giving the crude title compound which was p... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 275.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 307.0, "units": "MILLIGRAM"}}, "reaction_role": "REA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 22 ml of dry benzene there was added, under nitrogen atmosphere, 1.68 g (31.2 mMol) of sodium methoxide. There was then slowly added with stirring a solution of 6.06 g (30 mMol) of the 4-cyclohexyl aceto... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "benzene"}], "amount": {"volume": {"value": 22.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium methoxide"}], "amount": {"mass": {"value": 1.68, "units": "GRAM... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of methyl 7-methyl-3-oxochola-4,6-dien-24-oate (9) (0.62 g, 1.56 mmoles), 5% palladium on carbon (72 mg), 1,8diazobicyclo-[5.4.0]undec-7-ene (15 gl), cyclohexene (4.9 ml) and ethanol (3.6 ml) was ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N2"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 7-methyl-3-oxochola-4,6-dien-24-oate"}], "amount": {"mass": {"value": 0.62, "units": "GRAM"}}, "reaction_role": "REACT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Iodomethane (0.028 mL) is added to a suspension of N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-cinnolinecarboxamide; (Prep. 4, 0.16 g) and K2CO3 (0.20 g,) in 6 mL anhydrous DMF. The reaction is heated at 90° C. f... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 75.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Iodomethane"}], "amount": {"volume": {"value": 0.028, "units": "MILLILI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 0.30 g (1.68 mmol) 2,6-diethyl-4-hydroxy-benzaldehyde in 8 ml N,N-dimethylformamide in a pressure tube were added 0.16 ml (2.02 mmol) iodoethane and 0.35 g (2.52 mmol) potassium carbonate. ... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-diethyl-4-hydroxy-benzaldehyde"}], "amount": {"mass": {"value": 0.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "iodoethane"}], "amount": {"volume": {"value": 0.16, "units": "MILLI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Zinc powder (38 g) is added to warm solution (70°C) of the mono sodium salt of 5-nitro-4-phenoxy-3-sulfinobenzoic acid (10 g) in ethanol (190 ml), and while stirring 5 N hydrochloric acid (190 ml) is added ... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "mono sodium"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "5-nitro-4-phenoxy-3-sulfinobenzoic acid"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4M HCl in dioxane (1.2 ml) is added to a stirred solution of {4-[5-(2-amino-4-methyl-pyrimidin-5-yl)-2-chloro-benzenesulfonylamino]-cyclohexylmethyl}-carbamic acid tert-butyl ester (Example 3-17) (0.25 g, 0... | {"inputs": {"m1_m3_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "{4-[5-(2-amino-4-methyl-pyrimidin-5-yl)-2-chloro-benzenesulfonylamino]-cyclohexylmethyl}-carbamic acid tert-butyl ester"}], "amount": {"mass": {"value"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 14.25 g (0.068 moles) sample of ethyl 4H-cyclopenta[b]thiophene-6-carboxylate, the product of Example 1g., and 13.92 g p-(methylthio)benzoyl chloride were dissolved in 410 ml of dry nitromethane and place... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "SnCl4"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 4H-cyclopenta[b]thiophene-6-carboxylate"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAM... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (prepared as in Example 1, 8 g, 25.3 mmol) in dry tetrahydrofuran (100 mL) was added diisobutylaluminum hyd... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester"}], "amount": {"mass": {"value": 8.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diisobutylaluminum hydride"}], ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Cesium carbonate (8.23 g, 25.3 nmol) is added to a solution of 2-(2-Fluoro-phenoxy)-3-(4-hydroxy-phenyl)-2-methyl-propionic acid ethyl ester (2.68 g, 8.43 mmol) and toluene-4-sulfonic acid 2-[1-(4-methoxy-b... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant mixture"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a 500 ml round-bottomed flask, 0.088 mol of the compound obtained in Step A is dissolved in 0.881 ml of trifluoroacetic acid. The solution is cooled to 0° C. with the aid of an ice bath and 0.220 ml of t... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"moles": {"value": 0.088, "units": "MOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trifluoroacetic acid"}], "amount": {"volume": {"value": 0.881, "units": "MILLILITER"}}, "reactio... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Sodium (50 mg.) is added to 2-cyanopyrazine (1 gram, 0.01 mole) in 20 ml. of methanol. The solution is allowed to stand 1 hour at room temperature and is added to a suspension of pyrazine carboxylic acid hy... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
14 ml of nitrobenzene are cooled in an ice-bath and then mixed in succession with 3.8 g of AlCl3 and 3.7 g of 5-methyl-hexanoyl chloride in 5 mi of nitrobenzene. The mixture is stirred and then treated with... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "nitrobenzene"}], "amount": {"volume": {"value": 14.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title product 72 was prepared from 17-[3-(2-isopropylaminothiazol-4-yl)-6-methoxyisoquinolin-1-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo-[13.3.0.04,6]octadec-7-ene-4-carboxylic acid (71) follo... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-[17-(3-chloro-6-methoxyisoquinolin-1-yloxy)-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl]-(cyclopropyl)sulfonamide"}], "reaction_role": "REACTANT"}]}, "m0_m1": {"components": [{"identifiers": [{"type": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Using the procedure of Example 15, 1.6 g of 1,2,2-trimethyl-3-(2-propenyl)-cyclopentanol and 10 ml of acetyl chloride were reacted to obtain 1.3 of (1R,S) 1,2,2-trimethyl-1-acetyloxy-3-(2-propenyl)-cyclopen... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1,2,2-trimethyl-3-(2-propenyl)-cyclopentanol"}], "amount": {"mass": {"value": 1.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "acetyl chloride"}], "amount": {"volume": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(R)-N-(4-(3-Aminopiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide hydrochloride (0.112 g, 0.248 mmol; Example 29, Step C), 1-bromo-2-fluoroethane (0.0222 mL, 0.298 mmol) and DIE... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-N-(4-(3-Aminopiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide hydrochloride"}], "amount": {"mass": {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 319 mg (0.596 mmol) of 2-chlorobenzenesulfonic acid 1-[[1-N-(tert-butoxycarbonyl)piperidin-4-yl]methoxy]naphthalen-3-yl ester, as prepared in the preceding step, in 2 mL of methylene chlori... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chlorobenzenesulfonic acid 1-[[1-N-(tert-butoxycarbonyl)piperidin-4-yl]methoxy]naphthalen-3-yl ester"}], "amount": {"mass": {"value": 319.0, "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 the procedure described in Example 1E using the product from Example 6A and 1-isocyanato-3-trifluoromethyl-benzene instead of the product from Example 1D and 1-fluoro-2... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-isocyanato-3-trifluoromethyl-benzene"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "... |
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