Cyclohexanecarboxylic acid → N-[4-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl]cyclohexanecarboxamide

Participants

Reaction Steps

Ethyl chloroformate (87 mg) was added dropwise to a solution of cyclohexanecarboxylic acid (90 mg) and triethylamine (232 mg) in anhydrous N,N-dimethylformamide (8 ml) at ambient temperature. The mixture was stirred at the same temperature for 1.5 hours. To the reaction mixture was added 5-{4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione dihydrochloride (400 mg) in small portions. The mixture was stirred at 50° C. for 1.5 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. On addition of ethyl acetate to the residue insoluble product was formed and isolated by filtration and washed with ethyl acetate to give the title compound (262 mg).

Provenance & Evidence