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Pyridine → N-[3-(3-{3-Phenylpropyl}-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide

HRID 428849
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HRID 428849 반응식
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH:14]3[CH:12]([CH:13]3[C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH:12]3[CH:14]([CH:13]3[C:16]3[CH:17]=[C:18]([NH:22][S:30]([CH3:29])(=[O:32])=[O:31])[CH:19]=[CH:20][CH:21]=3)[CH2:15]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 221411543-[3-(3-Phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine

생성물 1

HCID 22141129N-[3-(3-{3-Phenylpropyl}-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide수율 71.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-[3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine (Preparation 25, 34 mg, 0.11 mmol) in dichloromethane (2 ml) at 0° C. under nitrogen was added pyridine (20 μl, 0.24 mmol) then methanesulfonylchloride (13 mg, 10 μl, 0.11 mmol). The mixture was allowed to warm to room temperature and was stirred for 1.5 hours. The mixture was concentrated in vacuo and the residue was purified by silica (5 g) column chromatography eluting with 80:20:1 ethyl acetate:hexane:ammonia solution (0.880). Product-containing fractions were combined and concentrated in vacuo to give the title compound as a pale yellow oil (29 mg, 71%).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica (5 g) column chromatography
  3. washeluting with 80:20:1 ethyl acetate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-acd589fc4b204c6db630fe79e1d9c665
출처 데이터셋
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06313312B1

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