Water → 3-(1-cyanocyclopropyl)-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}benzamide

HRID 1874576

반응식

HRID 1874576 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:28])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4([C:26]#[N:27])[CH2:25][CH2:24]4)[CH:18]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[CH3:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.O>N1C=CC=CC=1>[C:26]([C:23]1([C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=2)[C:16]([NH:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][C:5]3[CH:6]=[N:7][C:2]([NH:1][S:36]([C:33]4[CH:34]=[CH:35][C:30]([CH3:29])=[CH:31][CH:32]=4)(=[O:38])=[O:37])=[CH:3][CH:4]=3)[CH:10]=2)=[O:28])[CH2:24][CH2:25]1)#[N:27]

참가 물질

5

반응물 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 68416693N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide

생성물 1

HCID 684178753-(1-cyanocyclopropyl)-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}benzamide수율 92.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

To a solution of N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide (2.0 g, 5.4 mmol) in pyridine (60 mL) was added 4-methylbenzenesulfonyl chloride (1.13 g, 5.94 mmol) under ice-cooling, and the mixture was stirred with heating at 80° C. for 2 days. The reaction mixture was cooled to room temperature, water (200 mL) was added thereto, and the mixture was extracted with ethyl acetate (400 mL). The organic layer was washed with saturated brine (200 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate and diisopropyl ether to give the title compound (2.61 g, 92%) as a colorless solid.

후처리

  1. temperaturecooling
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionthe mixture was extracted with ethyl acetate (400 mL)
  4. washThe organic layer was washed with saturated brine (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe obtained residue was washed with ethyl acetate and diisopropyl ether

출처 및 근거

ORD 기록
ord-6b517e668f5d481eaeb6a8997f19bfed
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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