Dichloromethane → 1-(3-Phenylpyrid-6-ylmethyl)-5-(4-cyanobenzyl) imidazole hvdrochloride salt

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-phenyl-6-hydroxymethylpyridine (192 mg, 1.04 mmol) and diisopropylethylamine (0.360 mL, 2.07 mmol) in dichloromethane (8 mL) at -78° C. was added trifluoromethanesulfonic anhydride (0.180 mL, 1.07 nmuol) and the mixture stirred at -78° C. for 1 hour. To this mixture was added a solution of 1-trityl-4-(4-cyanobenzyl)imidazole (441 mg, 1.04 mmol) in dichloromethane (9 mL). The mixture was allowed to warm to ambient temperature and stirred for 4 hours. The solvent was evaporated in vacuo. The residue was dissolved in methanol (10 mL), heated at reflux for 1 hour, and the solvent evaporated in vacuo. The residue was partitioned between dichloromethane and sat. aq. NaHCO3 solution. The organic layer was dried, (Na2SO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, EtOAc and then 5% 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. FAB HRMS exact mass calcd for C23H19N4 351.160972 (MH+); found 351.161206.

Provenance & Evidence