Water → N-(3-{3-[3-(5-Fluoro-3-methyl-1H-indol-2-yl)propyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

HRID 1826388노트

반응식

HRID 1826388 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH2:12][C:13]([N:15]1[CH2:20][CH:19]3[CH:17]([C:18]3([C:22]3[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=3)[CH3:21])[CH2:16]1)=O)=[C:5]2[CH3:33].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][CH2:12][CH2:13][N:15]1[CH2:20][CH:19]3[CH:17]([C:18]3([C:22]3[CH:23]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=3)[CH3:21])[CH2:16]1)=[C:5]2[CH3:33]

참가 물질

7

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 22141190N-(3-{3-[3-(5-fluoro-3-methyl-1H-indol-2-yl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

생성물 1

HCID 22141356N-(3-{3-[3-(5-Fluoro-3-methyl-1H-indol-2-yl)propyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide수율 97.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-(3-{3-[3-(5-fluoro-3-methyl-1H-indol-2-yl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 128, 100 mg, 0.213 mmol) in anhydrous tetrahydrofuran (2.5 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.42 ml, 0.42 mmol) and the reaction mixture was stirred at room temperature overnight. The rapidly stirred reaction mixture was treated sequentially with water (0.45 ml), sodium hydrogen carbonate (450 mg) and ethyl acetate (10 ml). After 5 min, the reaction mixture was filtered and concentrated in vacuo to afford 95 mg of a colourless oil. This was purified by chromatography using a Biotage Flash 12™ cartridge packed with silica gel (8 g) eluting with hexane:ethyl acetate (100:0 to 0:100 over 30 min) then ethyl acetate:methanol (100:0 to 0:100 over 15 min) to afford the title compound as a white foam (56 mg, 46%).

후처리

  1. customThe rapidly stirred reaction mixture
  2. waitAfter 5 min
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d1a98a18352345c09dae863003d0074d
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049444B2

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