Methanol → HCID 22467915, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-cyclopentyl-2-[4-(1H-imidazole-2-sulfonyl)-phenyl]-propionic acid ethyl ester (113.5 mg, 0.30 mmol) and 2-aminothiazole (45.3 mg, 0.45 mmol) in a solution of magnesium methoxide in methanol (7.4 wt. %, 0.86 mL, 0.60 mmol) was heated at 110° C. for 8 h. At this time, the reaction was cooled to 25° C., filtered through a plug of celite, and washed with ethyl acetate. The filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded the 3-cyclopentyl-2-[4-(1H-imidazole-2-sulfonyl)-phenyl]-N-thiazol-2-yl-propionamide (24.7 mg, 19%) as a tan solid: mp 249-251° C.; EI-HRMS m/e calcd for C20H22N4O2S2 (M+) 430.1133 found 430.1133.

Provenance & Evidence