2-Aminothiazole → HCID 10223846, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-benzoylamino-phenyl)-3-cyclopentyl-propionic acid (20.2 mg, 0.06 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (39.8 mg, 0.09 mmol), and 2-aminothiazole (9.0 mg, 0.09 mmol) in methylene chloride (2 mL) at 25° C. was treated with N,N-diisopropylethylamine (0.25 mL, 0.18 mmol). The reaction mixture was stirred at 25° C. for 16 h. At this time, the mixture was poured into water (50 mL) and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with a 1N aqueous hydrochloric acid solution (1×25 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded {N-{4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenyl}-benzamide (95%) as a white solid: mp 285-290° C.; EI-HRMS m/e calcd for C24H25N3O2S (M+) 419.1667, found 419.1667.

Provenance & Evidence