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 1533025ノート

反応式

HRID 1533025 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aaed6022f83049418fb8194afc1dd891
出典データセット
uspto-grants-2001_03
特許番号
US06207678B1

反応ノート

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