Xenon difluoride → trans-N-{[2-(3-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

HRID 1639860노트

반응식

HRID 1639860 반응식
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[N:3]1.[Xe](F)[F:20]>C(#N)C.C(OCC)(=O)C>[F:20][C:10]1[N:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[C:8]([C@@H:11]1[CH2:13][C@H:12]1[CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:7][CH:6]=[CH:5]2

참가 물질

5

반응물 2

HCID 83674Xenon difluorideHCID 59334573trans-N-{[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

생성물 1

HCID 59334602trans-N-{[2-(3-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide수율 12.9%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-{[(1R,2R)-2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide (100 mg, 0.411 mmol) in acetonitrile (4.1 mL) was added xenon difluoride (76.5 mg, 0.452 mmol), and the mixture was stirred at room temperature for 4 hr. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate is solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=50/50→100/0) and preparative TLC (methanol/ethyl acetate=10/90) to give the title compound (13.9 mg, yield 11%).

후처리

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane=50/50→100/0) and preparative TLC (methanol/ethyl acetate=10/90)

출처 및 근거

ORD 기록
ord-780d952311f74c1a93b3f27e421a2c67
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110585B2

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