3-Chlorobenzaldehyde → 3-Benzyl 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-(2-cyclohexylethoxymethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 397972Notes

Reaction equation

HRID 397972 reaction equation
[CH:1]1([CH2:7][CH2:8][O:9][CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=O.[NH2:33]/[C:34](/[CH3:43])=[CH:35]\[C:36]([O:38][CH2:39][CH2:40][C:41]#[N:42])=[O:37]>CC(O)C>[Cl:24][C:25]1[CH:26]=[C:27]([CH:28]2[C:35]([C:36]([O:38][CH2:39][CH2:40][C:41]#[N:42])=[O:37])=[C:34]([CH3:43])[NH:33][C:11]([CH2:10][O:9][CH2:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:12]2[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 136714102-Cyanoethyl 3-aminocrotonateHCID 15540595Benzyl 4-(2-cyclohexylethoxy)acetoacetate

Product 1

HCID 155405963-Benzyl 5-(2-cyanoethyl) 4-(3-chlorophenyl)-2-(2-cyclohexylethoxymethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

0.50 g (1.57 mmol) of benzyl 4-(2-cyclohexylethoxy)acetoacetate, 0.22 g (1.57 mmol) of 3-chlorobenzaldehyde and 0.24 g (1.57 mmol) of 2-cyanoethyl 3-aminocrotonate were stirred in 8 ml of 2-propanol under heating at 70° C. for 22 hours. After 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. customAfter 2-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-886c703d4d804ab6b1e5d0994172172e
Source dataset
uspto-grants-2003_08
Patent number
US06610717B2

Reaction notes

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