2-Cyanoethyl 3-aminocrotonate → 2-Cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(3-phenyl-2-propene-1-ylcarbamoyl)-1,4-dihydropyridine-3-carboxylate

HRID 1700332Notes

Reaction equation

HRID 1700332 reaction equation
[C:1]([C:4](=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[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].[NH2:25]/[C:26](/[CH3:35])=[CH:27]\[C:28]([O:30][CH2:31][CH2:32][C:33]#[N:34])=[O:29]>CC(O)C>[Cl:24][C:20]1[CH:19]=[C:18]([CH:17]2[C:4]([C:5](=[O:6])[NH:7][CH2:8][CH:9]=[CH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:1]([CH3:2])[NH:25][C:26]([CH3:35])=[C:27]2[C:28]([O:30][CH2:31][CH2:32][C:33]#[N:34])=[O:29])[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 136714102-Cyanoethyl 3-aminocrotonateHCID 541391202-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide

Product 1

HCID 701560722-Cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(3-phenyl-2-propene-1-ylcarbamoyl)-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

193 mg (0.568 mmol) of 2-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide and 87.6 mg (0.568 mmol) of 2-cyanoethyl 3-aminocrotonate were heated at 70° C. under stirring in 2.8 ml of 2-propanol overnight. 2-Propanol was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/2) to obtain the title compound.

Workup

  1. custom2-Propanol was evaporated under reduced pressure
  2. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-7808c4c0c637451ca39a9a72a09d332a
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

Loading…