1,2-Dichloroethane → 4-(3-Chlorobenzyloxy)-6-methoxycarbonyl-pyridine-2-carboxylic acid {2-[3-(4-cyanobenzyl)-3H-imidazol-4-yl]ethyl}-amide

Participants

Reaction Steps

The mono methyl ester of 4-(3-chlorobenzyloxy)-pyridine-2,6-dicarboxylic acid (0.236 g, 0.622 mmol) was dissolved in DMF (2 mL) and treated with EDC (0.125 g, 0.653 mmol), HOBT (0.080 g, 0.59 mmol), 4-cyanobenzylhistamine (0.141 g, 0.622 mmol) and the pH adjusted to 7.5 with NMM. After stirring overnight at ambient temperature, the reaction mixture was concentrated to remove the DMF, the residue partitioned between EtOAc and aq saturated NaHCO3 solution, the organic layer separated, washed with brine and dried (MgSO4). Filtration and concentration gave the crude product which was chromatographed on RP HPLC to give the title compound which was isolated as the HCl salt.

Provenance & Evidence