Triethylamine → [5-(4-Chloro-phenyl)-4-cyclopentylmethyl-2-(2-ethoxy-4-methoxy-phenyl)-4,5-dihydro-imidazol-1-yl]-(4-methyl-piperazin-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(4-chloro-phenyl)-4-cyclopentylmethyl-2-(2-ethoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride (50 mg, 0.105 mmol) in methylene chloride (2 mL) was added to a stirred mixture of 1-methylpiperazine (18 μL, 0.158 mmol) and triethylamine (29 μL, 0.210 mmol) in methylene chloride (3 mL) cooled to 0° C. The reaction mixture was stirred at room temperature for 30 min then concentrated in vacuo. Purification of the crude residue by preparative HPLC (Zorbax C18) gave [5-(4-chloro-phenyl)-4-cyclopentylmethyl-2-(2-ethoxy-4-methoxy-phenyl)-4,5-dihydro-imidazol-1-yl]-(4-methyl-piperazin-1-yl)-methanone (64 mg, 93%, white solids) as trifluoroacetic acid salt. HR-MS (ES, m/z) observed 539.2789, calculated for C30H40N4O3Cl [(M+H)+]539.2784.

Provenance & Evidence