2-Aminothiazole → HCID 10159539, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid (100 mg, 0.29 mmol) in dry N,N-dimethylformamide (2 ml,) was treated with O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (110 mg, 0.29 mmol), N,N-diisopropylethylamine (61 μL, 0.35 mmol), and 2-aminothiazole (45 mg, 0.44 mmol). The reaction mixture was stirred at 25° C. under nitrogen for 15 h. The reaction mixture was poured into a mixture of water and ethyl acetate (1:1), and the layers were separated. The organic layer was washed with a 1N aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 2/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-N-thiazol-2-yl-propionamide (92 mg, 74%) as a white foam: mp 202-204° C.; FAB-HRMS m/e calcd for C27H26N2OS (M+H)+ 427.1844, found 427.1837.

Provenance & Evidence