3-Chlorobenzaldehyde → 5-(3-(Pyridine-3-yl)-2-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 890147Notes

Reaction equation

HRID 890147 reaction equation
[NH2:1]/[C:2](/[CH3:11])=[CH:3]\[C:4]([O:6][CH2:7][CH2:8][C:9]#[N:10])=[O:5].[C:12]([O:18][CH2:19][CH:20]=[CH:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[Cl:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH:32]=O>CC(O)C>[Cl:28][C:29]1[CH:30]=[C:31]([CH:32]2[C:13]([C:12]([O:18][CH2:19][CH:20]=[CH:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[O:17])=[C:14]([CH3:16])[NH:1][C:2]([CH3:11])=[C:3]2[C:4]([O:6][CH2:7][CH2:8][C:9]#[N:10])=[O:5])[CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 136714102-Cyanoethyl 3-aminocrotonateHCID 538744373-(Pyridin-3-yl)prop-2-en-1-yl 3-oxobutanoate

Product 1

HCID 695904045-(3-(Pyridine-3-yl)-2-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

387 mg (2.51 mmol) of 2-cyanoethyl 3-aminocrotonate, 547 mg (2.49 mmol) of (3-(pyridine-3-yl)-2-propene-1-yl) acetoacetate, and 0.285 ml (2.51 mmol) of 3-chlorobenzaldehyde were heated at 80° C. under stirring in 20 ml of 2-propanol overnight. 2-Propanol was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (chloroform/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 (chloroform/methanol=100:1)

Sources & evidence

ORD record
ord-7ffa00ef51a24c85a6a8f5d25622a744
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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