1,2-Dichloroethane → 1-(4-Cyanobenzyl)-5-(4'-phenylbenzamido)ethyl-imidazole

Participants

Reaction Steps

To a solution of 1-(4-cyanobenzyl)-5-aminoethylimidazole (107 mg, 0.358 mmol), 4-phenylbenzoic acid (70.9 mg, 0.358 mmol), 3-hydroxy-1,2,3-benzotriazin-4(3H)-one, (72.6 mg, 0.445 mmol) and triethylamine (0.215 mL, 1.54 mmol) in DMF (4.0 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, EDC, (83.3 mg, 0.435 mmol) and the mixture stirred for 16 hours at ambient temperature. The reaction was partitioned between sat. aq. NaHCO3 solution and EtOAc. The organic layer was dried, (Na2SO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 5% MeOH in CH2Cl2) to afford the imidazole which was converted to the HCl salt by treatment with one equivalent of HCl in aqueous acetonitrile. Evaporation of the solvent in vacuo afforded the title compound as a white solid.

Provenance & Evidence