Ammonia → 3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl methyl 2,6-dimethyl-4-(3-chloro-2-fluorophenyl)-1,4-dihydropyridine 3,5-dicarboxylate

HRID 483207Notes

Reaction equation

HRID 483207 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:11][O:12][C:13](=[O:18])[CH2:14][C:15]([CH3:17])=O.[NH2:19]/[C:20](/[CH3:39])=[CH:21]\[C:22]([O:24][CH2:25][C:26]([CH3:38])([CH3:37])[CH2:27][N:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:29])=[O:23].N>>[CH3:39][C:20]1[NH:19][C:15]([CH3:17])=[C:14]([C:13]([O:12][CH3:11])=[O:18])[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=2[F:10])[C:21]=1[C:22]([O:24][CH2:25][C:26]([CH3:38])([CH3:37])[CH2:27][N:28]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH3:29])=[O:23]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 7757Methyl acetoacetateHCID 7363353-Chloro-2-fluorobenzaldehydeHCID 13504496HCID 13504496, compound

Product 1

HCID 103696763-(N-benzyl-N-methylamino)-2,2-dimethylpropyl methyl 2,6-dimethyl-4-(3-chloro-2-fluorophenyl)-1,4-dihydropyridine 3,5-dicarboxylate

Procedure

To a solution of 158.5 mg of 3-chloro-2-fluorobenzaldehyde and 116 mg of methylacetoacetate in 1 ml of 2-pranol was added 291 mg of 3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl 3-aminocrotonate. To the mixture was added 0.1 ml of concentrated aqueous ammonia. The resulting maxture was refluxed for 9 hours. The solvent was distilled off under reduced pressure. The residue was chromatographed over silica gel to give the desired compound (156) with the identical physical properties to those of the compound in the Example 18-(i).

Workup

  1. temperatureThe resulting maxture was refluxed for 9 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-e5592e0de6b54522b7d3038ff4a4ce76
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

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