1H-Benzotriazole-1-carboxaldehyde → N-(3,5-Dimethylphenyl)-2-(2-formylaminopyridin-4-ylmethylthio)pyridine-3-carboxamide
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][S:9][C:10]2[C:15]([C:16]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=3)=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=1.[CH:27](N1C2C=CC=CC=2N=N1)=[O:28]>O1CCCC1.ClCCl>[CH3:26][C:21]1[CH:20]=[C:19]([NH:18][C:16]([C:15]2[C:10]([S:9][CH2:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:1][CH:27]=[O:28])[CH:7]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:17])[CH:24]=[C:23]([CH3:25])[CH:22]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
2-(2-Aminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide (the free base of Compound No. 3-1, 50 mg, 0.14 mmol) was dissolved in anhydrous tetrahydrofuran (0.20 mL), a solution of N-formylbenzotriazole (19 mg, 0.13 mmol) in anhydrous tetrahydrofuran (0.2 mL) was added thereto, and then the mixture was refluxed for 16 hours. The mixture was diluted with dichloromethane (15 mL), and then the whole was washed with 2 N aqueous sodium hydroxide solution (4.0 mL) twice and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 60 mg of the target compound quantitatively as a colorless solid.
Workup
- temperaturethe mixture was refluxed for 16 hours
- washthe whole was washed with 2 N aqueous sodium hydroxide solution (4.0 mL) twice
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-3518cd16b42c4a00abe5bedc6bc9f4f3
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07544703B2
Reaction notes
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