instruction stringlengths 151 5.17k | output stringlengths 291 4.64k |
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Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4-hydroxybenzaldehyde (4.04 g, 33.08 mmol), in acetonitrile (50 ml) was added K2CO3 (10.1 g), followed by N-(2-chloroethyl)morpholine hydrochloride (6.16 g). The reaction mixture was heated... | {"inputs": {"m1_m6_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-hydroxybenzaldehyde"}], "amount": {"mass": {"value": 4.04, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "K2CO3"}], "amount": {"mass": {"value": 10.1, "units": "GRAM"}}, "reaction_role": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of trans-2,7-diazabicyclo[4.4.0]decane (1.4 g, 10 mmoles), 37% aqueous formaldehyde solution (0.6 ml, 8 mmoles) and 0.5 g of palladium on charcoal (10%) was hydrogenated for 10 hours at 60° C. und... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "trans-2,7-diazabicyclo[4.4.0]decane"}], "amount": {"mass": {"value": 1.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "formaldehyde"}], "amount": {"volume": {"value": 0.6, "units": "MILLIL... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The above bis(4-fluorophenyl)(pyridin-4-yl)methanol (0.73 g, 2.45 mmol) was hydrogenated (60 pounds per square inch) in the presence of platinum oxide (0.1 g) catalyst in acetic acid (15 mL) for 6 hours at ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "bis(4-fluorophenyl)(pyridin-4-yl)methanol"}], "amount": {"mass": {"value": 0.73, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In stage (b) there are loaded into the second tubular reaction zone the 2,4-dichloro-6-isopropylamino-s-triazine coming from stage (a), ethylamine and sodium hydroxide to produce 2-chloro-4-ethylamino-6-iso... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,4-dichloro-6-isopropylamino-s-triazine"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ethylamine"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAM... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture consisting of 6-hydroxy-α-methyl carbazole-2-acetic acid ethyl ester (5.0 g, 0.021 mol), potassium hydroxide (5.0 g, 0.089 mol), methanol (300 mL), and water (20 mL) is refluxed for 15 hours. The ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "6-hydroxy-\u03b1-methyl carbazole-2-acetic acid ethyl ester"}], "amount":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a flask were added 1.0 g 6-methyl-N-(6-methylpyridin-2-yl)pyridin-2-amine, 0.84 g of pulverized potassium hydroxide and 15 ml of N,N-dimethylformamide. After stirring for 1 hour under nitrogen, the mixtu... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "6-methyl-N-(6-methylpyridin-2-yl)pyridin-2-amine"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium hydroxide"}], "amount": {"mass": {"value": 0.8... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
57.63 g (0.2 mole) of 4-(2,6-dichloroanilino)-3-thiophencarboxylic acid (dissolved in 350 ml of tetrahydrofuran) are added dropwise to a suspension of 7.59 g (0.2 mole) of lithium aluminum hydride in 170 ml... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2,6-dichloroanilino)-3-thiophencarboxylic acid"}], "amount": {"volume": {"value": 350.0, "units": "MILLILITER"}}, "re... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
According to the procedure described in Example 1(a), a mixture of 3(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-[2-hydroxy-1(S)-(hydroxymethyl)-2-methylpropyl]succinamic acid benzyl ester (137 mg, 0.26 mmol) i... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-[2-hydroxy-1(S)-(hydroxymethyl)-2-methylpropyl]succinamic acid benzyl ester"}], "amount": {"mass": {"value": 137.0, "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:
A solution of 6-phenylhexanoic acid (19.8 mmoles) in sieve dried tetrahydrofuran (5 ml) and reduced with diborane in tetrahydrofuran (30 ml, 29.1 mmoles) at 0° C. for 4 hours to give 6-phenylhexanol. To an ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "bromide"}], "amount": {"moles": {"value": 8.0, "units": "MILLI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Ethyl trifluoroacetate (1.90 g, 14 mmol) was dissolved in ether (15 mL) and treated with sodium methoxide (25%) (3.67 g, 17 mmol). To the stirred solution was added 3-coumaranone (1.50 g, 11 mmol). The reac... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium methoxide"}], "amount": {"mass": {"value": 3.67, "units": "GRAM"}}, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a manner analogous to that described in Example 11, by the reaction of ethyl 2-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride with 5-chloro-2-(2-methoxyethoxy)-benzoyl chloride (m.p. 49°-51° C.), the... | {"inputs": {"m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "5-chloro-2-(2-methoxyethoxy)-benzoyl chloride"}], "reaction_role": "REACTANT"}]}}, "conditions": {"con... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 5-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole (15.65 g, 41.7 mmol) and 4-{[(4-hydroxy-2-methylphenyl)methylamino]methyl}-2-methyl benzoic acid, methyl ester (12.49 g, 4... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-triazole"}], "amount": {"mass": {"value": 15.65, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-{[(4-hydroxy-2-methylphenyl)met... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
0.10 g (0.24 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 50 mg (0.26 mmol) 5,6-difluoro-2,3-di-hydro-1H-indole, 0.10 mL... | {"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "6-(2\u2032-oxo-1,1\u2032,2\u2032,3-tetrahydrospiro[indene-2,3\u2032-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride"}], "amount": {"mass": {"value": 0.1, "units": "GRAM"}}, "reaction_role": "REACTANT"},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
An aqueous slurry of calcium carbonate was prepared by charging a 300 mL reaction flask equipped with a stirrer with 10.0 g (100 mmol) of calcium carbonate (Escalon #2300 (average particle size, 1.7 μm), av... | {"inputs": {"m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "calcium carbonate"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"mass": {"value": 90.0, "units": "GRAM"}}, "reaction_role": "SOLVENT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Acetyl-4-methoxycyclohexanone (1.02 g) and cyanoacetamide (0.462 g) were added to 5 ml of ethanol. After adding a small amount of piperidine, the mixture was heated under reflux for 2 hours. Deposited cry... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Acetyl-4-methoxycyclohexanone"}], "amount": {"mass": {"value": 1.02, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "cyanoacetamide"}], "amount": {"mass": {"value": 0.462, "units": "GRAM"}}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
50 mg of 6-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)nicotinamide was reacted with 1-methyl-1,4-diazepane via Procedure F. The reaction was evaporated to dryness and purified on reverse phase HPLC to yield ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "6-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)nicotinamide"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-methyl-1,4-diazepane"}], "reaction_role": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 13.18 g of (2R,3R)-N,N-bis-(tert-butoxycarbonylmethyl)-2,3-epoxybutyramide in 100 ml of tetrahydrofuran is cooled with stirring to -15°, and 100 ml of a 0.5-molar solution of lithium hexamethy... | {"inputs": {"m7": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "SOLVENT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium hexamethyldisilazide"}],... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 20-mL resealable tube was charged with 2,4-dibromo-1-methyl-1H-imidazole (0.480 g, 2.00 mmol) and piperazine (3.4 g, 39.5 mmol), and the resulting mixture was stirred for 3 h at 130° C. The reaction mixtu... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2,4-dibromo-1-methyl-1H-imidazole"}], "amount": {"mass": {"value": 0.48, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "piperazine"}], "amount": {"mass": {"value": 3.4, "units": "GRAM"}}, "reac... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared according to general working method I from 1-[3-(3-iodo-phenoxy)-propyl]-pyrrolidine (124 mg, 0.37 mmol) and 5-(4-chloro-phenyl)-2-ethynyl-pyridine (80 mg, 0.37 mmol).
### ORD JSON:
| {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-[3-(3-iodo-phenoxy)-propyl]-pyrrolidine"}], "amount": {"mass": {"value": 124.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(4-chloro-phenyl)-2-ethynyl-pyridine... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Into a Round bottom flask was added Ethanone, 1-(2-hydroxy-4-methoxyphenyl)-ethanone (40.01 g, 0.241 mol), ethyl bromoacetate (28.17 mL, 0.2540 mol), potassium carbonate (69.6 g, 0.504 mol), and N,N-Dimethy... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethanone"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-(2-hydroxy-4-methoxyphenyl)-e... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The general procedure of Example 9 was repeated using 2,3-difluoro-4-ethoxyphenol and 4-bromomethyl-1-n-heptyl-1-phenyl-1-silacyclohexane, thereby obtaining the intended compound.
### ORD JSON:
| {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,3-difluoro-4-ethoxyphenol"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-bromomethyl-1-n-heptyl-1-phenyl-1-silacyclohexane"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditi... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a nitrogen-degassed mixture of 6-bromo-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester (3.27 g, 10.0 mmol), lithium bromide (2.58 g, 30.0 mmol), (1,3-diisopropylimidazo... | {"inputs": {"m1_m2_m5_m8_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "6-bromo-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester"}], "amount": {"mass": {"value": 3.27, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A suspension of [5-(4-fluoro-phenyl)-2-methylsulfanyl-oxazol-4-yl]-methanol (4.15 g; 17.34 mmol) in dry toluene (100 ml) was treated with 2,2,2-trifluoroethanol (12.63 ml; 173.4 mmol), 1,1'-(azodicarbonyl)d... | {"inputs": {"m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "[5-(4-fluoro-phenyl)-2-methylsulfanyl-oxazol-4-yl]-methanol"}], "amount": {"mass": {"value": 4.15, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 100.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In the same manner as in Starting Material Synthesis Example 60 and using 2-bromo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid, thionyl chloride and 2-amino-5-methylthiophenol, 2-bromo-4,5,6,7-tetr... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-bromo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "thionyl chloride"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"i... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of ethyl 2-(11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-12-yl)-2-hydroxyacetate (233 mg, 0.325 mm... | {"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2-(11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2\u2032,3\u2032:5,6][1,3]oxazino[3,4-a]indol-12-yl)-2-hydroxyacetate"}], "amount": {"mass": {"value": 233.0, "uni... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of the 4,5-dihydro-imidazole of step 2 (1.5 g, 3.8 mmol) and p-toluenesulfonic acid monohydrate (0.30 g, 1.5 mmol) in toluene (250 ml) was heated to reflux for 40 hours. An additional p-toluenesul... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4,5-dihydro-imidazole"}], "amount": {"mass": {"value": 1.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "p-toluenesulfonic acid monohydrate"}], "amount": {"mass": {"value": 0.3, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of ethyl 2-ethoxycarbonyl-4-(4-nitrophenyl)-4-oxobutyrate (6.2 g, 19 mmol) and sulphuric acid (1.0 g) in acetic acid:water (4:1, 50 ml) was stirred at reflux for 4 hours, then concentracted in va... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2-ethoxycarbonyl-4-(4-nitrophenyl)-4-oxobutyrate"}], "amount": {"mass": {"value": 6.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sulphuric acid"}], "amount": {"mass": {"value": 1.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of monoethyl 5-[(4-fluorophenyl)-methyl]-1,3-benzenedipropanoate (3.0 g), diphenyl-phosphoryl azide (2.51 g) and triethylamine (1.3 ml) in dry t-butanol (25 ml) was stirred at room temperature fo... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "monoethyl 5-[(4-fluorophenyl)-methyl]-1,3-benzenedipropanoate"}], "amount": {"mass": {"value": 3.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diphenyl-phosphoryl azide"}], "amount": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4-(hydroxymethyl)-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane (10.0 g, 0.062 mol) in 200 mL of acetone is added Jones reagent (chromium trioxide and sulfuric acid) until an orange color persi... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(hydroxymethyl)-1-methyl-2,6,7-trioxabicyclo[2.2.2]octane"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Jones reagent"}], "reaction_role": "REACTANT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
As described for example 114k, 6-(5-methyl-3-pyrimidin-4-yl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid (38 mg, 0.12 mmol) was converted, using 2-amino-2-methyl-1-propanol instead of ethanolamine, to... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "6-(5-methyl-3-pyrimidin-4-yl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid"}], "amount": {"mass": {"value": 38.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
5-bromo-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoic acid (2.0 g, 0.0058 mol) was dissolved in DMSO (20 mL) and 3-(aminomethyl)-4-isopropyl-6-methylpyridin-2(1H)-one (2.1 g, 11.7 mmol) and triet... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "PyBOP"}], "amount": {"mass": {"value": 4.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(aminomethyl)-4-isopropyl-6-methylpyridin-2(1H)-one"}], "amount": {"mass": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 3-(quinolin-2-yl)cyclobutanecarboxylic acid (200 mg, 0.800 mmol, as prepared above) in DCM was cooled to 0° C. and treated with 10 μL of DMF followed by oxalyl chloride (154 μL, 1.76 mmol). Th... | {"inputs": {"m6_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "HBr"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 0.35, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3_m4_m5": {"components": [{"identifiers": [{"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 1-(quinolin-6-yl)hydrazine hydrochloride (4.0 g, 20.5 mmol) and 4,4-dimethyl-3-oxo-pentanenitrile (3.6 g, 30 mol) in EtOH (50 mL) and conc. HCl (5 mL) was heated at reflux overnight. After remo... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(quinolin-6-yl)hydrazine hydrochloride"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4,4-dimethyl-3-oxo-pentanenitrile"}], "amount": {"mass": {"va... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of 33 (212 mg, 0.80), Cs2CO3 (260 mg, 0.80) in DMF (15 ml), 39 (200 mg, 0.89 mmol) was added portionwise and the mixture was stirred at room temperature for 2 days. H2O (30 ml) was added and... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "33"}], "amount": {"mass": {"value": 212.0, "units": "MILLIGRAM"}}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To the mixture of 2-(2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)acetic acid 193-2 (25 mg, 0.1 mmol) and 5-(pyridazin-3-yl)pyridin-2-amine 145-3 (17 mg, 0.1 mmol) in DCM (1 mL) was added N,N′-Diisopropylcarbodii... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(2\u2032-fluoro-3-methyl-2,4\u2032-bipyridin-5-yl)acetic acid"}], "amount": {"mass": {"value": 25.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "5-(pyridazin-3-yl)pyridin-2-amine"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2,5-di-tert-butyl-4-methoxyphenol (9 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 ml). Cesium carbonate (13 mmol) and 1-bromoethyl methyl ether (9 mmol) were added to the solution. The reactio... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2,5-di-tert-butyl-4-methoxyphenol"}], "amount": {"moles": {"value": 9.0, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 10.0, "unit... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of propargylamine (6.4 g, 71.2 mmol) in pyridine (100 mL) was added benzylchloroformate (13.37 g, 78.2 mmol) in 100 mL CH2Cl2 over 0.5 h. The reaction was stirred for 16 h and the volatiles we... | {"inputs": {"m1_m3_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "propargylamine"}], "amount": {"mass": {"value": 6.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzylchloroformate"}], "amount": {"mass": {"value": 13.37, "units": "GRAM"}}, "reactio... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Following the procedure described above for the synthesis of compound 28 (Scheme 8) but substituting 1,3-propanediol (27) for 1,2-ethanediol (34), title compound 35 was obtained in 61% yield [Romero-Salguer... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "compound 28"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1,2-ethanediol"}], "reaction_role": "SOLVENT"}]}}, "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:
A mixture of (R)-3-(5-acetoxyhexyl)-7,8-dihydro-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (700 mg, 2.0 mmol) and a 1.0 M solution of hydrogen chloride in diethyl ether (5 ml, 5.0 mmol) in methanol ... | {"inputs": {"m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrogen chloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "amount": {"volume": {"value": 5... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A stirred mixture of 2-fluoro-4-iodoaniline (5.0 g, 21.1 mmol), CuI (90 mg, 0.42 mmol), and PdCl2(PPh3)2 (300 mg, 0.42 mmol) in a pressure tube was flushed with argon. Ethynyltrimethylsilane (2.28 g, 23.2 m... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Et2O"}], "reaction_role": "SOLVENT"}]}, "m1_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "2-fluoro-4-iodoaniline"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"t... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 0.757 g (3.4 mmol) of trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene and 0.970 g (3.1 mmol) of methyl rac-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro[1,3-dithiolane-2,4'-naphthalene]-2'-carb... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "trans-1,2-diacetoxy-1,2-dihydrobenzocyclobutene"}], "amount": {"mass": {"value": 0.757, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl rac-1',2',3',4',5',8'-hexahydro-5',8'-dioxospiro... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The bromide 58 (300 mg, 0.46 mmol) was added to a microwave reaction tube containing copper(I) cyanide (124 mg, 1.38 mmol) in NMP. The capped reaction tube was placed in a microwave reactor and the mixture ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "bromide"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "copper(I) cyanide"}], "amount": {"mass": {"value": 124.0, "units": "M... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 15 grams 4-hydroxy-3-methoxyphenylacetonitrile (91.91 mmol), 26.40 ml (33.59 grams) n-butyl bromide (245 mmol) and 21.17 grams potassium carbonate (153.2 mmol) in 150 ml acetone was heated to r... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-hydroxy-3-methoxyphenylacetonitrile"}], "amount": {"mass": {"value": 15.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "n-butyl bromide"}], "amount": {"volume": {"value": 26.4, "units... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
6-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amine (4-3; 0.244 g, 0.470 mmol) and 300 mg 10% palladium on carbon was stirred in 10 ml EtOH. Hydrogenate und... | {"inputs": {"m1_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "6-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amine"}], "amount": {"mass": {"value": 0.244, "units": "GRAM"}}, "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:
Following General Procedure A, 1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide (Compound 8, 40 mg, 0.092 mmol) in DMF (1.0 ml) was reacted with K2CO3 (38 mg, 0.28 mmol), cyclop... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide"}], "amount": {"mass": {"value": 40.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Com... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4,5-dimethylbenzene-1,2-diamine (39 mg, 0.286 mmol) was added to a mixture of (2R,4R)-1-(tert-butoxycarbonyl)-4-(3-(4-cyanophenyl)ureido)piperidine-2-carboxylic acid (100 mg, 0.258 mmol), BOP (120 mg, 0.27 ... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4,5-dimethylbenzene-1,2-diamine"}], "amount": {"mass": {"valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a similar manner to Example 87, (2S,4S)-1-[[N-[4-carboxybicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg) and 3,3-dimethylbutylamine (45.8 μL) were used to obtain (2S,4S)-... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(2S,4S)-1-[[N-[4-carboxybicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In 50 ml of THF was dissolved 4.99 g of N-benzyloxycarbonyl-L-proline and then 2.23 g of triethylamine was added to the solution. Then, after slowly adding thereto 2.39 g of ethyl chloroformate under ice-co... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "n-butylamine"}], "amount": {"mass": {"value": 2.19, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m5_m1": {"components": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
51 g. of 4-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-methanol (0.24 mol.) and 300 ml. of n-butylamine are heated at 100° in an autoclave for seven hours. After cooling, the surplus butylamine is removed b... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-methanol"}], "amount": {"moles": {"value": 0.24, "units": "MOLE"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "n-butylamine"}], "reaction_rol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 500-mL round-bottom flask was charged with 2-(bromomethyl)-3-methyloxirane (42.4 g, 280 mmol), methanol (120 mL), and diphenylmethanamine (44 mL, 260 mmol), and the resulting solution stirred overnight at... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(bromomethyl)-3-methyloxirane"}], "amount": {"mass": {"value": 42.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diphenylmethanamine"}], "amount": {"volume": {"value": 44.0, "units": "M... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2,6-Dichloro-3-nitropyridine (71-1, 10 g, 51.8 mmol, 1.0 equiv) was added to anhydrous DCM (207 mL) and cooled to −15° C. TEA (7.57 mL, 53.9 mmol, 1.04 equiv) was then added followed by allyl amine (4.05 mL... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-Dichloro-3-nitropyridine"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 207.0, "units": "MILLILITER"}}, "reacti... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1-[4-(5-Cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine (1.1 g) was dissolved in benzyl alcohol (10 ml) under inert gas atmosphere at 20-25° C. To the clear solution was added HCl in isopr... | {"inputs": {"m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1-[4-(5-Cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine"}], "amount": {"mass": {"value": 1.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzyl alcohol"}], "amount": {"vol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Oxalyl chloride (2.60 g) was added to a suspension of 2-chloro-4-fluorobenzoic acid (3.44 g) in dichloromethane (50 ml). Two drops of dimethylformamide were added and the mixture was stirred for 18 hours at... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "reaction_role": "CATALYST"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Oxalyl chloride"}], "amount": {"mass": {"value": 2.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2,5-Dibromopyrimidine and 4-octyloxybenzeneboronic acid are reacted analogously to Example 1 to give 5-bromo-2-(4-octyloxyphenyl) pyrimidine. ##STR34##
### ORD JSON:
| {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2,5-Dibromopyrimidine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-octyloxybenzeneboronic acid"}], "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:
2.56 mmol of 2,2-dimethyl-4,6-dioxo-5-[3-[(triphenylmethyl)thio]propyl]-1,3-dioxane-5-propanoic acid methyl ester (II) (1.4 g) with 18 mmol of sodium hydroxide (0.72 g) was dissolved in a mixture of 5 ml of... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2,2-dimethyl-4,6-dioxo-5-[3-[(triphenylmethyl)thio]propyl]-1,3-dioxane-5-propanoic acid methyl ester"}], "amount": {"mass": {"value": 1.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "s... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Bromo-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridine (1.0 g, 3.3 mmol, from Example 21a), tert-butyl (2R)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (0.67 g, 3.3 mmol), Pd(OAc)2 (14.8 mg, 0.066 mmol),... | {"inputs": {"m1_m2_m6_m3_m4_m10": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Bromo-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)pyridine"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert-butyl (2R)-2-(hydroxymethyl)pyr... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1 g of 4-hydroxycyclohexanecarboxylic acid (6.94 mmol, 1 eq.) is placed in 50 mL of a 4/1 mixture of toluene and methanol. 5.55 mL of trimethylsilyldiazomethane (11.10 mmol, 1.6 eq.) are added dropwise to t... | {"inputs": {"m1_m4_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-hydroxycyclohexanecarboxylic acid"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 5 ml of N-methylpyrrolidone were added 1.8 g of 4-(t-butylamino)-2-chloro-5-fluoropyrimidine and 4.0 g of benzylamine, and the mixture was stirred at 140° C. for 17 hours and separated by adding 300 ml o... | {"inputs": {"m3_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(t-butylamino)-2-chloro-5-fluoropyrimidine"}], "amount": {"mass": {"value": 1.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzylamine"}], "amount": {"mass": {"value": 4.0, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
36.3 g of 3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]-pyrimidine-2,4-dione, 23 g of 1-chloro-2-methylsulfanylethane (97% pure), 17.4 g of lithium bromide and 27 g of ethyldiisopropylamine in 700 ml of dime... | {"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]-pyrimidine-2,4-dione"}], "amount": {"mass": {"value": 36.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-chloro-2-methylsulfanylethane"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of 2-chloro-3-[(2-thiazolyl)carbonyl]pyridine (257.5 mg, 1.2 mmol, 1 equiv) in dioxane (3 mL) in a sealed tube was added hydrazine (2 mL). The mixture was heated at 150° C. overnight, cooled... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant residue"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m4": {"components": [{"id... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Reflux for 5 hours with stirring a mixture of 1.20 g (0.00417 moles) of (S)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1-H-3-benzazepine (obtained in step E of Example 1), 2.0 ml (0.017 moles) ... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-7-chloro-8-hydroxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1-H-3-benzazepine"}], "amount": {"mass": {"value": 1.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzoyl chloride"}], "am... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of isopropyl 5-allyloxy-2(S)-(tert-butoxycarbonylamino)pentanoate (product of step 26D, 16.1 g, 51.1 mmol) and lithium hydroxide hydrate (4.19 g, 102 mmol) in THF/water (100 mL/20 mL) was stirred ... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "isopropyl 5-allyloxy-2(S)-(tert-butoxycarbonylamino)pentanoate"}], "amount": {"mass": {"value": 16.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "product"}], "reaction_role": "REACTANT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 4-methoxy-1-phenyl-1H-pyrazolo[4,3-c]pyridin-3-yl trifluoromethanesulfonate (100 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (83 mg), tetrakis(triphenylphosphine)pal... | {"inputs": {"m1_m2_m6_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-methoxy-1-phenyl-1H-pyrazolo[4,3-c]pyridin-3-yl trifluoromethanesulfonate"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-(4,4,5,5-tetra... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Phthalimide (1.47 g, 10 mmol) was added to a mixture of glacial acetic acid (15 mL), concentrated hydrochloric acid (7 mL), and tin powder (2.97 g). The slurry was heated at reflux for 2 h. After this time ... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Phthalimide"}], "amount": {"mass": {"value": 1.47, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 7.0, "units": "MILLILITER"}}, "react... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2M aqueous sodium hydroxide (2.446 mL, 4.89 mmol) was added in one portion to methyl 4-[4-(2-adamantylcarbamoyl)-5-ethylsulfanyl-pyrazol-1-yl]benzoate (Intermediate #99) (430 mg, 0.98 mmol) in methanol (20 ... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 2.446, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl 4-[4-(2-adamantylcarbamoyl)-5-ethylsulfanyl-pyrazol-1-yl]benzoate"}]... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 4-picoline (280 g, 3.0 moles), p-methoxy benzaldehyde (410 g, 3.0 moles) and 500 ml. acetic anhydride is refluxed for 24 hours, cooled, evaporated in vacuo, and the residue taken up in water an... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-picoline"}], "amount": {"mass": {"value": 280.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "p-methoxy benzaldehyde"}], "amount": {"mass": {"value": 410.0, "units": "GRAM"}}, "reaction_rol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution containing 950 mg eq) of 4-[6-(2,6-diamino-4-hydroxypyrimidin-5-yl)hex-1-en-3-yl]benzoic acid as prepared in step F, 351 mg (1.2 eq) Of N-methylmorpholine, and 10.0 ml of anhydrous dimethylformam... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N-methylmorpholine"}], "amount": {"mass": {"value": 351.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "N-methylmorpholine"}], "amount": {"mass": {"value": 351.0,... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of glycine methyl ester hydrochloride (16.24 g, 116.31 mmol) and Et3N (16.21 mL, 116.31 mmol) in MeOH were added a solution of benzyl 1-formylcyclopropylcarbamate (5.10 g, 23.26 mmol) in MeOH ... | {"inputs": {"m1_m2_m5_m3_m6_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "glycine methyl ester hydrochloride"}], "amount": {"mass": {"value": 16.24, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Et3N"}], "amount": {"volume": {"value": 16.21, "units": "MI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 4-chloro-6-nitrothieno[2,3-d]pyrimidine (prepared as disclosed in Bull. Chim. Soc. Fr. 1975, 3-4, Pt. 2, 592) (500 mg, 2.3 mmol), 1-(4-methoxyphenyl)ethanamine HCl (513 mg, 2.8 mmol), and triet... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-6-nitrothieno[2,3-d]pyrimidine"}], "amount": {"mass": {"value": 500.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-(4-methoxyphenyl)ethanamine HCl"}], "amount": {"mass"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 1 liter 5-necked round bottom flask is fitted with a mechanical stirrer, a Dean-Stark trap topped with a nitrogen padded reflux condenser, and a thermocouple attached to a temperature controller. A mixtur... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1,2-dibromotetrafluoroethane"}], "amount": {"mass": {"value": 155.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m6_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "DMSO"}], "amount": {"volume": {"value": 450.0, "un... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of (1S,2R)-4′-(4-chlorophenyl)-2-(methoxymethyl)-2′,3′,9′-trimethylspiro[cyclopropane-1,6′-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine] (2.35 g, 5.69 mmol) in DCM (70 mL) at −78° C. was ... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "reaction_role": "REACTANT"}]}, "m2_m7_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(1S,2R)-4\u2032-(4-chlorophenyl)-2-(methoxymethyl)-2\u2032,3\u2032,9\u2032-trimethylspiro[cyclopropane-1,6\u2032-thieno[3,2-... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 0.10 mole of 2-(piperazin-1-yl)-4-amino-6-chloro-7-methoxyquinazoline in 300 ml. of methanol is added with vigorous stirring, 0.10 mole of 2,3-dihydro-4H-benzopyran-2-carboxylic acid chloride. After the ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(piperazin-1-yl)-4-amino-6-chloro-7-methoxyquinazoline"}], "amount": {"moles": {"value": 0.1, "units": "MOLE"}}, "reaction_role": "REACTANT"}]}, "m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2,3-dihydro-4H-benzopyran-... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 4-isobutyl-3-(trifluoromethyl)benzoic acid (Preparation 23A, 0.55 g, 2.234 mmol) in dichloromethane (5 mL) and methanol (2.00 mL) was added trimethylsilyldiazomethane (1.452 mL, 2.90 mmol) at 0° C. The r... | {"inputs": {"m1_m3_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-isobutyl-3-(trifluoromethyl)benzoic acid"}], "amount": {"mass": {"value": 0.55, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trimethylsilyldiazomethane"}], "amount": {"volume": {"valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Under argon 6.63 g of magnesium (273 mmol) was suspended in 15 mL of tert-butyl methyl ether. A solution of 38.68 g of methyl iodide (273 mmol) in 145 mL of tert-butyl methyl ether was added during 45 minut... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl methyl ether"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m2_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl iodide"}], "amount": {"mass": {"value": 38.6... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a 100 mL round-bottomed flask was added 4-aminobenzenethiol (4.9 g, 39.1 mmol) and potassium carbonate (9.72 g, 70.3 mmol) in dimethylformamide (20 ml). tert-Butyl 4-(tosyloxy)piperidine-1-carboxylate (5... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-aminobenzenethiol"}], "amount": {"mass": {"value": 4.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 9.72, "units": "GRAM"}}, "reacti... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 3,5-dimethyl-4-iodopyrazole (200.0 mg, 0.9008 mmol), ((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (515.9 mg, 1.802 mmol), K2CO3 (136.9 mg, 0.9909 mmol), 1,4,7,10,13,16-h... | {"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3,5-dimethyl-4-iodopyrazole"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfo... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 6′-hydroxy-4,4-dimethyl-4,5-dihydro-3H-[1,3′]bipyridinyl-2,6-dione (468 mg, 2.00 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic acid 5-benzoylamino-pyridin-2-yl ester (0.90 ... | {"inputs": {"m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "6\u2032-hydroxy-4,4-dimethyl-4,5-dihydro-3H-[1,3\u2032]bipyridinyl-2,6-dione"}], "amount": {"mass": {"value": 468.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-(tert-butyl-dime... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 4-bromo-3-fluorotoluene (35 g) and sodium hydroxide (7.7 g) in pyridine and water was stirred and heated to reflux. Potassium permanganate (123 g) was added to the mixture over 2 hours. The re... | {"inputs": {"m1_m2_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-bromo-3-fluorotoluene"}], "amount": {"mass": {"value": 35.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"mass": {"value": 7.7, "units": "GRAM"}}, "re... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (5.6 g.), mesyl chloride (6.9 g.), pyridine (15 ml.) and methylene ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate"}], "reaction_role": "REACT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (1.7 g) and trimethyl orthoacetate (1.2 ml) in the presence of pyridinium para-toluenesulfonate (0.16 g) were heated in ... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1,1-Dimethylethyl 7-amino-8-hydroxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate"}], "amount": {"mass": {"value": 1.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trimethyl orthoa... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a flask were added 2.0 g 2-mercapto-5-methylbenzimidazole, 4.2 g potassium carbonate, 30 ml N,N-dimethylformamide and 3.9 g benzyl chloride. The reaction mixture was heated to 60 C for 16 hours, then coo... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-mercapto-5-methylbenzimidazole"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 4.2, "units": "G... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a mixture of 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-iodo-1H-imidazole in DCM was added ethylmagnesium bromide at −78° C. The temperature of the mixture was allowed to warm up to about 10° C.... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-iodo-1H-imidazole"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAM... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To the title A compound, (4-methanesulfonyl-phenyl)-methanesulfonic acid, sodium salt is added PCl5 (10 g) in 200 mL of chloroform and the mixture is stirred for 48 h. The solids are filtered off, the chlor... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(4-methanesulfonyl-phenyl)-methanesulfonic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "PCl5"}], "amount": {"m... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Into a 500-mL 3-necked round-bottom flask, was placed ethyl 2-(4-fluorophenyl)quinazoline-4-carboxylate (15 g, 50.63 mmol, 1.00 equiv), oxolane (150 mL), lithiumol (2.4 g, 100.22 mmol, 2.00 equiv) and water... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2-(4-fluorophenyl)quinazoline-4-carboxylate"}], "amount": {"mass": {"value": 15.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "oxolane"}], "amount": {"volume": {"v... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 417 mg (1 mMol) of N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide in 50 ml of methanol are added 100 mg of 5% palladium on carbon. The mixture is hy... | {"inputs": {"m1_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide"}], "amount": {"mass": {"value": 417.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
AlCl3 (1.46 g, 10.98 mmol) was added to a solution of 4-(2-fluoro-4-nitrophenoxy)pyrrolo[1,2-b]pyridazine (600 mg, 2.19 mmol) in dichloroethane (60 mL). After stirring at room temperature for 1 hour and add... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "AlCl3"}], "amount": {"mass": {"value": 1.46, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"ty... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture 3-chloro-5-methylphenylacetonitrile (13.3 g; from step (ii) above) and KOH (17 g; 0.3 mol) in 150 mL of water:i-PrOH (2:1) was heated while stirring in an autoclave at 120° C. overnight and then a... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-chloro-5-methylphenylacetonitrile"}], "amount": {"mass": {"value": 13.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "KOH"}], "amount": {"mass": {"value": 17.0, "units": "GRAM"}}, "react... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
40 g (20.4 mmol) of geranil acetate was dissolved in 100 ml of n-hexane. After adding 17.1 g (70.0 mmol) of trichloroisocyanuric acid slowly, the mixture was maintained at −10° C. to 0° C. for six hours. Af... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "acetate"}], "amount": {"mass": {"value": 40.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "n-hexane"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVE... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 2-(3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (Example 62; 20 mg, 0.046 mmol) in THF (460 μL, 0.046 mmol) was a... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride"}], "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of piperidin-4-ylmethanol (2.19 g) in DMSO (40 mL) were added 4-fluoro-3-(trifluoromethyl)benzonitrile (3.00 g) and potassium carbonate (3.21 g). The reaction mixture was stirred at 100° C. fo... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "piperidin-4-ylmethanol"}], "amount": {"mass": {"value": 2.19, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a manner similar to the method described in Examples 42c, rac-(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-[2-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propyl]-pyrrolidine... | {"inputs": {"m3_m4_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine"}], "amount": {"mass": {"value": 0.36, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HATU"}], "amount": {"mass": {"value": 0.84, "units... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine (0.3 g.), ethyl formate (5 ml.) and EtOH (2 ml.) was heated under reflux for 48 hours, then evaporated to dryness. The resi... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine"}], "amount": {"mass": {"value": 0.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl formate"}], "amount": {"volum... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Pd(PPh3)4 (10 mg, 0.009 mmol) was added to a solution of 3-(5-bromofuran-2-yl)-5-fluoro-benzonitrile (180 mg, 86% purity, 0.59 mmol) and 2-trimethylstannylpyridine (193 mg, 0.80 mmol) in toluene (2.5 mL) un... | {"inputs": {"m4_m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(5-bromofuran-2-yl)-5-fluoro-benzonitrile"}], "amount": {"mass": {"value": 180.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-trimethylstannylpyridine"}], "amount": {"mass": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of methyl 3-nitro-5-(trifluoromethyl)benzoate (Reference Example 27, 24.6 g, 98.9 mmol) in ethanol (1500 mL) was sparged in a Parr bottle with nitrogen for 10 min. After this time, 10 wt % Pd/C (... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Pd/C"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 3-nitro-5-(trifluoromethyl)benzoate"}], "amount": {"mass": {"value": 24.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a mixture of N-hydroxy-4-(trifluoromethoxy)benzimidoyl chloride (1.2 g, 5 mmol) and methyl propiolate (0.9 mL, 10 mmol) in toluene (12 mL) was added Et3N (0.73 mL, 5.3 mmol) dropwise over 10 minutes. The... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N-hydroxy-4-(trifluoromethoxy)benzimidoyl chloride"}], "amount": {"mass": {"value": 1.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl propiolate"}], "amount": {"volume": {"value": 0... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Aminophenyldimethyl carbinol from Step 1 was reductively alkylated with 1-t-butyloxycarbonyl-4-piperidinone (2.6 g, 13.2 mmol) by the procedure given in Step 2 of Example 1 to give 4-(2-(1-methyl-1-hydrox... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Aminophenyldimethyl carbinol"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-t-butyloxycarbonyl-4-piperidinone"}], "amount": {"mass": {"value": 2.6, "units": "GRAM"}}, "reaction_role":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 9.8 g of guanidine free base and 13.8 g of 2-methoxy-3-carboethoxy-5-[t-butyl(dimethyl)silyloxymethyl]-3,4,5,6-tetrahydropyridine was heated at 90° C. under nitrogen for 18 hours. The mixture w... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "guanidine"}], "amount": {"mass": {"value": 9.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-methoxy-3-carboethoxy-5-[t-butyl(dimethyl)silyloxymethyl]-3,4,5,6-tetrahydropyridine"}], "amount... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Analogous to the procedure used to prepare Example 5(b), 4-chloro-6-(4-trifluoromethylphenyl)pyrimidine, Example 5(a), (200 mg, 0.77 mmol) and 3-methylsulphonylaniline hydrochloride (80 mg, 0.39 mmol, Acros... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-6-(4-trifluoromethylphenyl)pyrimidine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-methylsulphonylaniline hydrochloride"}], "amount": {"mass": {"value": 80.0, "units": "MILLIGRAM"}}, "reaction_ro... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)-furo[3,2-c]pyridin-6-ylamine (10.0 mg, 0.0237 mmol), 2-fluorophenyl isocyanate (0.00597 g, 0.0436 mmol), DIPEA (... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)-furo[3,2-c]pyridin-6-ylamine"}], "amount": {"mass": {"value": 10.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAM... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A flask was charged with 7-chloroimidazo[1,2-c]pyrimidin-5(6H)-one (Preparation H, 1.02 g, 6.00 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (Prepa... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Pd2dba3"}], "amount": {"mass": {"value": 0.549, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "Et2O"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m4": {"components": [{"iden... |
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