Piperidine → 5-Cyano-4-(4-cyanophenyl)-2-imino-n,n,6-trimethyl-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-3-pyridinecarboxamide

HRID 639160Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639160
[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]([N:32]([CH3:34])[CH3:33])=[O:31])#[N:28].N1CCCCC1>C(O)C>[C:12]([C:11]1[CH:17]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH:29]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])[C:27](=[NH:28])[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]=1[CH3:14])#[N:13]

Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 2511432-Cyano-N,N-dimethylacetamideHCID 50752873-{[3-(Trifluoromethyl)phenyl]amino}but-2-enenitrile

Produkt 1

HCID 211101395-Cyano-4-(4-cyanophenyl)-2-imino-n,n,6-trimethyl-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-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 49.57 mg (0.44 mmol) 2-cyano-N,N-dimethylacetamide 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. After cooling down to room temperature, the crude product is purified by column chromatography with cyclohexane/ethyl acetate 20:1, 10:1, 8:1, 6:1, 4:1, 2:1, 1:1, 1:2 and dichloromethane/methanol 100:1, 50:1, 20:1 as eluents. The product containing fractions are repurified by preparative HPLC.

Aufarbeitung

  1. temperatureat reflux overnight
  2. customthe crude product is purified by column chromatography with cyclohexane/ethyl acetate 20:1, 10:1, 8:1, 6:1, 4:1, 2:1, 1:1, 1:2 and dichloromethane/methanol 100:1, 50:1, 20:1 as eluents
  3. additionThe product containing fractions
  4. customare repurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0d92f01fd9a4436a9f15ceb6cfef1f41
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691854B2

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