Acetic Acid → HCID 178420137, compound
Reaction equation
C[O-].[Na+].[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)#[N:5].C(O)(=O)C.[N:16]1([CH2:23][C:24]2[S:25][C:26]([C:29]([NH:31][NH2:32])=O)=[CH:27][CH:28]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CO>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[NH:32][N:31]=[C:29]([C:26]2[S:25][C:24]([CH2:23][N:16]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:28][CH:27]=2)[N:5]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
81 mg (1.5 mmol) of sodium methoxide was added to 13.5 ml of methanol solution containing 1.56 g (15.0 mmol) of 2-cyanopyridine and stirred at room temperature for 3.5 hours. The reaction mixture was ice-cooled, 0.085 ml (1.5 mmol) of acetic acid and 1.52 g (6.0 mmol) of 2-(hexahydro-1H-azepin-1-yl)methylthiophene-5-carboxylic acid hydrazide were added with ice-cooling, and then the mixture was stirred at room temperature for 24 hours. The thus precipitated crystals were collected by filtration to give 1.97 g of the crystals. A 894 mg (2.5 mmol) portion of them was dissolved in 13 ml of acetic acid and heated under reflux for 6.5 hours. The solvent was evaporated, 28% aqueous ammonia and chloroform were added, and then the thus separated organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated and the resulting residue was purified by a silica gel column chromatography to give 715 mg of the title compound.
Workup
- temperaturecooled
- temperaturecooling
- stirringthe mixture was stirred at room temperature for 24 hours
- filtrationThe thus precipitated crystals were collected by filtration
Sources & evidence
- ORD record
- ord-c40b325474fd47aa9cf21cd0ae3f0292
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090804
Reaction notes
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