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1-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butane → 4-Cyclohexyl-1-(3-[3,4-dichlorophenyl]-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonate

HRID 844541
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HRID 844541 반응식
[CH3:1][S:2]([O:5][CH2:6][CH2:7][CH:8]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=1)[CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])(=[O:4])=[O:3].[CH:33]1([C:39]23[CH2:46][CH2:45][N:42]([CH2:43][CH2:44]2)[CH2:41][CH2:40]3)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>C(#N)C>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH:33]1([C:39]23[CH2:46][CH2:45][N+:42]([CH2:6][CH2:7][CH:8]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=4)[CH2:9][N:10]4[CH:14]=[CH:13][N:12]=[C:11]4[C:15](=[O:24])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22][CH3:23])([CH2:41][CH2:40]2)[CH2:43][CH2:44]3)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 226138281-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butaneHCID 226138404-Cyclohexylquinuclidine

생성물 1

HCID 226138324-Cyclohexyl-1-(3-[3,4-dichlorophenyl]-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonate수율 84.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butane (0.59 g) (see Preparation 84) and 4-cyclohexylquinuclidine (0.27 g) (see Preparation 1) were dissolved in acetonitrile (8 ml) and heated under reflux for 3.5 hours. The solvent was removed under reduced pressure and the resulting residue dissolved in dichloromethane and the solvent removed under reduced pressure. The residue was chromatographed on silica gel eluting with a solvent gradient of 95:5 changing to 85:15, by volume, dichloromethane:methanol to give 4-cyclohexyl-1-(3-[3,4-dichlorophenyl]-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonate (0.69 g) as a white foam.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 3.5 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe resulting residue dissolved in dichloromethane
  5. customthe solvent removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with a solvent gradient of 95:5 changing to 85:15, by volume, dichloromethane

출처 및 근거

ORD 기록
ord-c50aa8d1bd1d418e8b45599670a65e96
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06380396B1

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