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Water → HCID 22141139, 화합물

HRID 428851
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HRID 428851 반응식
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6]2.[CH2:24]([S:27](Cl)(=[O:29])=[O:28])[CH2:25][CH3:26].[OH2:31]>ClCCl>[C:21]([OH:28])(=[O:31])[CH3:22].[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:27]([CH2:24][CH2:25][CH3:26])(=[O:29])=[O:28])[CH:20]=[CH:21][CH:22]=2)[CH:3]2[CH:7]1[CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 962WaterHCID 662791-Propanesulfonyl chlorideHCID 11266768HCID 11266768, 화합물

생성물 1

HCID 22141139HCID 22141139, 화합물수율 4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-[6-methyl-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine (Preparation 8, 200 mg, 0.65 mmol) in pynidine (2 ml) under nitrogen at 0° C. was added n-propanesulfonyl chloride (140 mg, 0.98 mmol), then the mixture was stirred at room temperature for 16 hours. Water (5 ml) and dichloromethane (5 ml) were added, and the mixture was stirred for 30 minutes. The organic phase was washed further with water (5 ml) for 30 minutes, separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica (10 g) column chromatography eluting with ethyl acetate:hexane:ammonia solution (0.880) (20:80:1 then 50:50:1). Product-containing fractions were combined and concentrated in vacuo. The residue was further purified by preparative HPLC (condition 4). Combination and evaporation of appropriate fractions gave the title compound as a pale brown solid (11 mg, 4%).

후처리

  1. stirringthe mixture was stirred for 30 minutes
  2. washThe organic phase was washed further with water (5 ml) for 30 minutes
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica (10 g) column chromatography
  8. washeluting with ethyl acetate
  9. concentrationconcentrated in vacuo
  10. customThe residue was further purified by preparative HPLC (condition 4)
  11. customCombination and evaporation of appropriate fractions

출처 및 근거

ORD 기록
ord-a2c7ede328c142acb416f861f018cfd9
출처 데이터셋
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06313312B1

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