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 1533025Notes

Reaction equation

HRID 1533025 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aaed6022f83049418fb8194afc1dd891
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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