Triethylamine → HCID 18537676, compound

Participants

Reaction Steps

A mixture of 5-[4-[6-[2-(3-amino-4-t-butylphenyl)ethoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (0.40 g), α,α,α-trifluoro-p-tolyl isocyanate (0.13 g), triethylamine (0.13 g) and anhydrous N,N-dimethylformamide (8 ml) was stirred at room temperature for 24 hours and then at 60° C. for 2.5 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by preparative reverse phase high performance liquid chromatography using acetonitrile:water=57:43 containing triethylamine (2%) and acetic acid (2%) as the eluant to afford the title compound (0.24 g, mp 165-167° C.).

Provenance & Evidence