2-Aminothiazole → HCID 22467899, compound

Participants

Reaction Conditions

Reaction Steps

A solution of triphenylphosphine (59 mg, 0.22 mmol) in methylene chloride (1 mL) was cooled to 0° C. and then slowly treated with N-bromosuccinimide (39 mg, 0.22 mmol). The reaction mixture was stirred at 0° C. for 20 min and then treated with 3-cyclopentyl-2-(4-pyridin-4-yl-phenyl)-propionic acid (55 mg, 0.19 mmol). The resulting reaction mixture was stirred at 0° C. for 10 min and then allowed to warm to 25° C. where it was stirred for 20 min. The reaction mixture was then treated with 2-aminothiazole (41 mg, 0.41 mmol). The resulting reaction mixture was stirred at 25° C. for 15 h. The crude reaction mixture was then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 20/1 methylene chloride/methanol) to afford impure 3-cyclopentyl-2-(4-pyridin-4-yl-phenyl)-N-thiazol-2-yl-propionamide as an orange foam. The impure foam was treated with a solution of hexanes/ethyl acetate (5 mL, 1:3), and a precipitate formed. The reaction mixture was placed in the freezer for 15 h, and the solid was collected by filtration to afford 3-cyclopentyl-2-(4-pyridin-4-yl-phenyl)-N-thiazol-2-yl-propionamide (26 mg, 37%) as a pale orange solid: mp 213-215° C.; EI-HRMS m/e calcd for C22H23N3OS (M+) 377.1562, found 377.1564.

Provenance & Evidence