2-Cyanoethyl 3-aminocrotonate → 3-Benzyl 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1700360Notes

Reaction equation

HRID 1700360 reaction equation
[C:1]([C:5](=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=O)[CH2:2][CH3:3].[NH2:24]/[C:25](/[CH3:34])=[CH:26]\[C:27]([O:29][CH2:30][CH2:31][C:32]#[N:33])=[O:28]>CC(O)C>[Cl:23][C:19]1[CH:18]=[C:17]([CH:16]2[C:26]([C:27]([O:29][CH2:30][CH2:31][C:32]#[N:33])=[O:28])=[C:25]([CH3:34])[NH:24][C:1]([CH2:2][CH3:3])=[C:5]2[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 136714102-Cyanoethyl 3-aminocrotonateHCID 70155581HCID 70155581, compound

Product 1

HCID 701582763-Benzyl 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.00 g (3.08 mmol) of benzyl 2-propionyl-3-(3-chlorophenyl)acrylate (mixture of E:Z=1:1) and 475 mg (3.08 mmol) of 2-cyanoethyl 3-aminocrotonate were heated under reflux in 10 ml of 2-propanol at 80° C. 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-2ece5256c29d425ebcc152aee433b128
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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