Trimethylsilyl cyanide → N-(2-cyanocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide

HRID 602004

반응식

HRID 602004 반응식
C[Si]([C:5]#[N:6])(C)C.[F:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([F:27])[C:22]=1[O:23][CH2:24][C:25]#[CH:26])[C:11]([N:13]1[CH:19]2[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]2)=[O:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:5]([CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[NH:13][C:11](=[O:12])[C:10]1[CH:20]=[C:21]([F:27])[C:22]([O:23][CH2:24][C:25]#[CH:26])=[C:8]([F:7])[CH:9]=1)#[N:6]

참가 물질

5

반응물 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 577011787-[3,5-Difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane

생성물 1

HCID 57701183N-(2-cyanocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide수율 75.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

At room temperature, 99 mg of trimethylsilyl cyanide was added dropwise to a mixture of 12 ml of tetrahydrofuran and 291 mg of 7-[3,5-difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane and, further, tetrabutylammonium fluoride (0.05 ml of 1M tetrahydrofuran solution) was added. The resulting mixture was heated with stirring at 40° C. for 8 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.24 g of N-(2-cyanocyclohexyl)-3,5-difluoro-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 80 of the present invention) represented by the formula:

후처리

  1. temperatureThe resulting mixture was heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ce3839a163ca4d19bcead8b86f67c73b
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902400B2

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