Malononitrile → 2-Amino-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3,5-pyridinedicarbonitrile

HRID 639162Notes

Reaction equation

HRID 639162 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([CH3:14])=[CH:11][C:12]#[N:13])[CH:6]=[CH:7][CH:8]=1.[CH:17]([C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1)=O.[C:27](#[N:31])[CH2:28][C:29]#[N:30].N1CCCCC1>C(O)C>[NH2:31][C:27]1[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:15])([F:16])[F:1])[CH:4]=2)[C:10]([CH3:14])=[C:11]([C:12]#[N:13])[CH:17]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[C:28]=1[C:29]#[N:30]

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 50752873-{[3-(Trifluoromethyl)phenyl]amino}but-2-enenitrile

Product 1

HCID 684257822-Amino-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3,5-pyridinedicarbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon, 750 mg (3.32 mmol) of the compound of Example 2A, 434.79 mg (3.32 mmol) 4-formylbenzonitrile and 219.04 mg (3.32 mmol) malononitrile are dissolved in 5 ml ethanol. 28.23 mg (33 μl, 0.33 mmol) piperidine are added, and the mixture is stirred at reflux overnight. The product is crystallised from the reaction mixture at 0° C. The formed crystals are filtered, washed twice with cold ethanol and dried.

Workup

  1. temperatureat reflux overnight
  2. customThe product is crystallised from the reaction mixture at 0° C
  3. filtrationThe formed crystals are filtered
  4. washwashed twice with cold ethanol
  5. customdried

Sources & evidence

ORD record
ord-55295e84040343069f77af3aef68c500
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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