Methanol → 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid propylamide

Participants

Reaction Steps

A suspension of 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carbonyl chloride hydrochloride salt in acetonitrile (0.2 M, 0.10 mL) was added to a vial containing n-propylamine (0.2 M in toluene, 0.11 mL) and DIPEA (0.5M in toluene, 0.10 mL). After incubation on a shaker at ambient temperature overnight, the mixture was diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid propylamide: MS (m/z) 347.95 (M+1).

Provenance & Evidence