Cyanoacetamide → 2-Amino-5-cyano-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3-pyridinecarboxamide

HRID 639158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639158
[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]([CH2:29][C:30]([NH2:32])=[O:31])#[N:28].N1CCCCC1>C(O)C>[NH2:28][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:29]=1[C:30]([NH2:32])=[O:31]

Komponenten

6

Edukt 4

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 50752873-{[3-(Trifluoromethyl)phenyl]amino}but-2-enenitrile

Produkt 1

HCID 116042192-Amino-5-cyano-4-(4-cyanophenyl)-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-3-pyridinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Under argon, 100 mg (0.44 mmol) of the compound of Example 2A, 57.97 mg (0.44 mmol) 4-formylbenzonitrile and 37.17 mg (0.44 mmol) 2-cyanoacetamide are dissolved in 2 ml ethanol. 3.76 mg (4.4 μl, 0.04 mmol) piperidine are added and the mixture is stirred at reflux overnight. The product is crystallised from the reaction mixture at 4° C. The formed crystals are filtered, washed twice with ethanol and dried. The crude product is purified by column chromatography with dichloromethane/methanol 100:1 as eluent.

Aufarbeitung

  1. temperatureat reflux overnight
  2. customThe product is crystallised from the reaction mixture at 4° C
  3. filtrationThe formed crystals are filtered
  4. washwashed twice with ethanol
  5. customdried
  6. customThe crude product is purified by column chromatography with dichloromethane/methanol 100:1 as eluent

Quellen und Nachweise

ORD-Eintrag
ord-f5d232e4c9f1495998ea47d3e4c0c9c6
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691854B2

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