2-Cyanoethyl 3-aminocrotonate → 2-Cyanoethyl 2,6-dimethyl-4-(4-nitrophenyl)-5-[(3-phenyl-2-propene-1-yl)carbamoyl]-1,4-dihydropyridine-3-carboxylate

HRID 1700347Notes

Reaction equation

HRID 1700347 reaction equation
[C:1]([C:4](=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:5]([NH:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6])(=O)[CH3:2].[NH2:27]/[C:28](/[CH3:37])=[CH:29]\[C:30]([O:32][CH2:33][CH2:34][C:35]#[N:36])=[O:31]>CC(O)C>[CH3:37][C:28]1[NH:27][C:1]([CH3:2])=[C:4]([C:5](=[O:6])[NH:7][CH2:8][CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[C:29]=1[C:30]([O:32][CH2:33][CH2:34][C:35]#[N:36])=[O:31]

Participants

4

Reactant 2

HCID 136714102-Cyanoethyl 3-aminocrotonateHCID 53894018HCID 53894018, compound

Product 1

HCID 701576352-Cyanoethyl 2,6-dimethyl-4-(4-nitrophenyl)-5-[(3-phenyl-2-propene-1-yl)carbamoyl]-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

424 mg (1.21 mmol) of 2-acetyl-3-(4-nitrophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide and 187 mg (1.21 mmol) of 2-cyanoethyl 3-aminocrotonate were heated at 70° C. under stirring in 10 ml of 2-propanol for 2 days. 2-Propanol was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1) to obtain the title compound.

Workup

  1. custom2-Propanol was evaporated under reduced pressure
  2. customthe residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1)

Sources & evidence

ORD record
ord-77a83537bbfd464298e806535401838a
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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