Sodium triacetoxyborohydride → HCID 67234529, 화합물

HRID 75687노트

반응식

HRID 75687 반응식
C(O)(=O)/C=C\C(O)=O.[NH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[N:14]=[CH:13]2.[CH2:25]([N:32]1[CH2:37][CH:36]2[C:38](=O)[CH:33]1[CH2:34][CH2:35]2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:25]([N:32]1[CH2:37][CH:36]2[CH:38]([NH:9][C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[N:15]([C:19](=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22])[N:14]=[CH:13]4)[CH:33]1[CH2:34][CH2:35]2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 49759181N-Benzyl-2-azabicyclo[2.2.1]heptan-7-oneHCID 66716091HCID 66716091, 화합물

생성물 1

HCID 67234529HCID 67234529, 화합물수율 25%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(5-amino-1H-indazol-1-yl)-2,2-dimethylpropan-1-one maleate salt (580 mg, 1.7 mmol, prepared as described in U.S. Ser. No. 08/021,4614) and 2-benzyl-2-azabicyclo[2.2.1]heptan-7-one (250 mg, 1.7 mmol) (J. R. Malpass, S. Handa, and R. White, Org. Lett., 2005, 7, 2759-2762) in THF (9 mL) was added sodium triacetoxyborohydride (740 mg, 3.5 mmol), and the mixture was stirred at ambient temperature for 24 h. The reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate, and the organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue was purified by normal phase chromatography followed by reversed phase HPLC to afford 175 mg (25%) of 1-(5-((1SR,4SR,7RS)-2-benzyl-2-azabicyclo[2.2.1]heptan-7-ylamino)-1H-indazol-1-yl)-2,2-dimethylpropan-1-one.

후처리

  1. customThe reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by normal phase chromatography

출처 및 근거

ORD 기록
ord-83bc017d7f1942caafe96998ef1adcd1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835457B2

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