1-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butane → 4-(3,5-Dimethylphenyl)-1-(3-[3,4-dichlorophenyl]-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonate

HRID 1533025노트

반응식

HRID 1533025 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].[CH3:33][C:34]1[CH:35]=[C:36]([C:41]23[CH2:48][CH2:47][N:44]([CH2:45][CH2:46]2)[CH2:43][CH2:42]3)[CH:37]=[C:38]([CH3:40])[CH:39]=1>C(#N)C>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH3:40][C:38]1[CH:37]=[C:36]([C:41]23[CH2:46][CH2:45][N+:44]([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])([CH2:47][CH2:48]2)[CH2:43][CH2:42]3)[CH:35]=[C:34]([CH3:33])[CH:39]=1

참가 물질

4

반응물 2

HCID 226138281-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butaneHCID 226138314-(3,5-Dimethylphenyl)quinuclidine

생성물 1

HCID 226137924-(3,5-Dimethylphenyl)-1-(3-[3,4-dichlorophenyl]-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonate수율 87.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butane (0.55 g) (see Preparation 84) and 4-(3,5-dimethylphenyl)quinuclidine (0.28 g) (see Preparation 12) were dissolved in acetonitrile (10 ml) and heated under reflux for 2.5 hours. The solvent was removed under reduced pressure, 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 90:10, by volume, dichloromethane:methanol to give 4-(3,5-dimethylphenyl)-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 2.5 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 90:10, by volume, dichloromethane

출처 및 근거

ORD 기록
ord-aaed6022f83049418fb8194afc1dd891
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06207678B1

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