2-Aminothiazole → HCID 10114125, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-[4-(2-thiophen-2-yl-acetylamino)-phenyl]-propionic acid (76.6 mg, 0.21 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (142.0 mg, 0.32 mmol) and 2-aminothiazole (32.1 mg, 0.32 mmol) in methylene chloride (1 mL) at 25° C. was treated with triethylamine (0.9 mL, 0.64 mmol). The reaction mixture was stirred at 25° C. for 16 h. This mixture was then poured into water (50 mL) and extracted with methylene chloride (2×25 mL). The combined organic extracts were washed with a 1N aqueous sodium hydroxide solution (1×25 mL), a 1N aqueous hydrochloric acid solution (1×25 mL), water (1×25 mL), and a saturated aqueous sodium chloride solution (3×25 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate) afforded 3-cyclopentyl-N-thiazol-2-yl-2-[4-(2-thiophen-2-yl-acetylamino)-phenyl]-propionamide (82.7 mg, 87.8%) as a tan solid: mp 220-221° C.; EI-HRMS m/e calcd for C23H25N3O2S2 (M+) 4391388, found 439.1379.

Provenance & Evidence