Dichloromethane → 1-(2-(3-Trifluoromethoxyphenyl)-pyrid-5-ylmethyl)-5-(4-cyanobenzyl)imidazole hvdrochloride salt

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3-trifluoromethoxyphenyl)-5-hydroxymethylpyridine (66 mg, 0.25 mmol), diisopropylethylamine (0.085 mL, 0.49 mmol), and 1-trityl-4-(4-cyanobenzyl)imidazole (105 mg, 0.25 mmol) in dichloromethane (1.4 mL) at -78° C. was added trifluoromethanesulfonic anhydride (0.041 mL, 0.25 mmol) and the mixture stirred at -78° C. for 1 hour. The reaction was allowed to warm to ambient temperature and stirred for 4 hours. The solvent was evaporated in vacuo. The residue was dissolved in methanol (15 mL), heated at reflux for 1 hour, and the solvent evaporated in vacuo. The residue was partitioned between dichloromethane and sat. aq. Na2CO3 solution. The organic layer was dried, (Na2SO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 3% MeOH in CH2Cl2). The amine was converted to the HCl salt by treatment with 1.0M HCl in aqueous acetonitrile. Evaporation of the solvent in vacuo afforded the title compound as a white solid.

Provenance & Evidence