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

HRID 844542
Notes
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Reaction equation

HRID 844542 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][CH:8]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=1)[CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15](=[O:27])[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:17]=1)(=[O:4])=[O:3].[CH:36]1([C:42]23[CH2:49][CH2:48][N:45]([CH2:46][CH2:47]2)[CH2:44][CH2:43]3)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C(#N)C>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH:36]1([C:42]23[CH2:49][CH2:48][N+:45]([CH2:6][CH2:7][CH:8]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=4)[CH2:9][N:10]4[CH:14]=[CH:13][N:12]=[C:11]4[C:15](=[O:27])[C:16]4[CH:21]=[CH:20][C:19]([F:22])=[C:18]([C:23]([F:24])([F:26])[F:25])[CH:17]=4)([CH2:44][CH2:43]2)[CH2:46][CH2:47]3)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 226138101-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(3-trifluoromethyl-4-fluorobenzoyl)imidazol-1-yl]butaneHCID 226138404-Cyclohexylquinuclidine

Product 1

HCID 226137974-Cyclohexyl-1-(3-[3,4-dichlorophenyl]-4-[2-(3-trifluoromethyl-4-fluorobenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonateYield 66.4%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

1-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(3-trifluoromethyl-4-fluorobenzoyl)imidazol-1-yl]butane (0.77 g) (see Preparation 80) and 4-cyclohexylquinuclidine (0.31 g) (see Preparation 1) were dissolved in acetonitrile (10 ml) and heated under reflux for 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 80:20, by volume, dichloromethane:methanol to give 4-cyclohexyl-1-(3-[3,4-dichlorophenyl]-4-[2-(3-trifluoromethyl-4-fluorobenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonate (0.69 g) as a white foam.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 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 80:20, by volume, dichloromethane

Sources & evidence

ORD record
ord-05e9432fda9a47ff8ff6676b1122fdac
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06380396B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes