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

HRID 483208Notes

Reaction equation

HRID 483208 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH2:11]/[C:12](/[CH3:31])=[CH:13]\[C:14]([O:16][CH2:17][C:18]([CH3:30])([CH3:29])[CH2:19][N:20]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:21])=[O:15].[C:32]([O:38][CH3:39])(=[O:37])[CH2:33][C:34]([CH3:36])=O>>[CH3:31][C:12]1[NH:11][C:34]([CH3:36])=[C:33]([C:32]([O:38][CH3:39])=[O:37])[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=2[F:10])[C:13]=1[C:14]([O:16][CH2:17][C:18]([CH3:30])([CH3:29])[CH2:19][N:20]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:21])=[O:15]

Participants

4

Reactant 3

HCID 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 were adde 291 mg or 3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl 3-aminocrotonate and 116 mg of methyl acetoacetate. The mixture was refluxed overnight. The solvent was distilled off in vacuo to give a residue. The reaction was treated in the same ways as the Example 18-(iii) to give the desired product (156) which has the identical physical properties with those of the compound of the Example 18-(i).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. distillationThe solvent was distilled off in vacuo
  3. customto give a residue

Sources & evidence

ORD record
ord-746774841d6744e0ac224a0b3a5088df
Source dataset
uspto-grants-1986_03
Patent number
US04578395

Reaction notes

Loading…