Water → N-[4-(1-cyano-cyclopropyl)-benzyl]-2,2,2-trifluoro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-acetamide

HRID 855186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855186
[H-].[Na+].[F:3][C:4]([F:21])([F:20])[C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)=[O:6].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([C:33]#[N:34])[CH2:32][CH2:31]2)=[CH:26][CH:25]=1.O>CN(C=O)C>[C:33]([C:30]1([C:27]2[CH:26]=[CH:25][C:24]([CH2:23][N:7]([CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=3)[C:5](=[O:6])[C:4]([F:20])([F:21])[F:3])=[CH:29][CH:28]=2)[CH2:31][CH2:32]1)#[N:34]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 18176503N-[3-(Trifluoromethyl)phenethyl]-2,2,2-trifluoroacetamideHCID 200354281-(4-(Bromomethyl)phenyl)cyclopropanecarbonitrile

Produkt 1

HCID 86603033N-[4-(1-cyano-cyclopropyl)-benzyl]-2,2,2-trifluoro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-acetamideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

20 mg (0.51 mmol) of a sodium hydride suspension in mineral oil (60%) were suspended in 4.2 ml DMF. At 0° C. 134 mg (0.42 mmol) of 2,2,2-trifluoro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-acetamide dissolved in 1 ml DMF were added dropwise and the reaction mixture was stirred for 30 min at 0° C. Then 100 mg (0.42 mmol) of 1-(4-bromomethyl-phenyl)-cyclopropanecarbonitrile dissolved in 1 ml DMF were added and the reaction mixture was stirred at 0° C. for 3 h. Water was added and the mixture was extracted twice with EtOAc. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (45 g silica gel; heptane/diethyl ether=1:1) to yield 135 mg (72%) of N-[4-(1-cyano-cyclopropyl)-benzyl]-2,2,2-trifluoro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-acetamide as a yellow viscous oil. MS (ISP) 458.4 (M+NH4)+. MS (ISP). 499.1 (M+OAc)−.

Aufarbeitung

  1. customAt 0° C
  2. additionwere added dropwise
  3. additionwere added
  4. stirringthe reaction mixture was stirred at 0° C. for 3 h
  5. extractionthe mixture was extracted twice with EtOAc
  6. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by column chromatography (45 g silica gel; heptane/diethyl ether=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-e9ddfaefa5694648997d2acf6c0c2fa2
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259183B2

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