Malononitrile → Ethyl 6-amino-5-cyano-4-(4-cyanophenyl)-2-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3-pyridinecarboxylate

HRID 1766348Notes

Reaction equation

HRID 1766348 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)[CH3:7])[CH3:2].[CH:20]([C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1)=O.[C:30](#[N:34])[CH2:31][C:32]#[N:33].N1CCCCC1>C(O)C>[NH2:34][C:30]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[CH:10]=2)[C:6]([CH3:7])=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:19])[CH:20]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[C:31]=1[C:32]#[N:33]

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 68427624Ethyl-3-{[3-(trifluoromethyl)phenyl]amino}-2-butenoate

Product 1

HCID 21110182Ethyl 6-amino-5-cyano-4-(4-cyanophenyl)-2-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound is prepared as described for Example 14A with 100 mg (0.37 mmol) of the compound of Example 1A, 48 mg (0.37 mmol) 4-formylbenzonitrile, 24.18 mg (0.37 mmol) malononitrile and 3.12 mg (3.6 μl, 0.04 mmol) piperidine in 2 ml ethanol. The product is purified by HPLC.

Workup

  1. customThe compound is prepared
  2. customThe product is purified by HPLC

Sources & evidence

ORD record
ord-f218822f779b456f8730e41c6add25ef
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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