홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Ethyl Acetate → N-(6-chloro-5-phenyl-1H-indazol-3-yl)butanamide

HRID 497649
노트
인쇄 미리보기

반응식

HRID 497649 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][C:33]=2[Cl:34])[N:30](COCC[Si](C)(C)C)[N:29]=[C:28]3[NH:43][C:44](=[O:48])[CH2:45][CH2:46][CH3:47])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C>O1CCCC1>[C:19]1([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][C:33]=2[Cl:34])[NH:30][N:29]=[C:28]3[NH:43][C:44](=[O:48])[CH2:45][CH2:46][CH3:47])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 22319494N-[5-phenyl-6-chloro 1-[(2-trimethylsilylethoxy)methyl]indazol-3-yl]butanamide

생성물 1

HCID 22319604N-(6-chloro-5-phenyl-1H-indazol-3-yl)butanamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
67 °C

실험 절차

8.8 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 650 mg of N-[5-phenyl-6-chloro-1-[[2-(trimethylsilyl]ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 25 cm3 of tetrahydrofuran. The medium is maintained at 67° C. for 20 hours and is then allowed to return to room temperature and 75 cm3 of ethyl acetate are added; the organic phase is washed with 75 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 2×75 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure (2 kPa; 45° C.). The residue is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.) and the residue is taken up in 15 cm3 of diisopropyl ether, filtered off on a sinter funnel and washed successively with 10 cm3 of diisopropyl ether and with 5 cm3 of ethyl acetate. After drying under reduced pressure (90 Pa; 50° C.), 240 mg of N-(5-phenyl-6-chloro-1H-indazol-3-yl)butanamide are obtained in the form of a white solid melting at 235° C.

후처리

  1. customto return to room temperature
  2. washthe organic phase is washed with 75 cm3 of saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure (2 kPa; 45° C.)
  6. customThe residue is purified by chromatography under an argon pressure of 50 kPa
  7. washon a column of silica gel (particle size 40-60 μm; diameter 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume)
  8. additionThe fractions containing the expected product
  9. customevaporated under reduced pressure (2 kPa; 50° C.)
  10. filtrationfiltered off on a sinter funnel
  11. washwashed successively with 10 cm3 of diisopropyl ether and with 5 cm3 of ethyl acetate
  12. dry with materialAfter drying under reduced pressure (90 Pa; 50° C.), 240 mg of N-(5-phenyl-6-chloro-1H-indazol-3-yl)butanamide

출처 및 근거

ORD 기록
ord-f1058de7707040d8b72b7bc81e4f730a
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06949579B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트