2-Aminothiazole → HCID 800397, compound

Participants

Reaction Steps

To a solution of 2-(4-Chloro-phenoxy)-2-methyl-propionic acid (0.3 g, 1.4 mmol) in DCM (10 ml) was added triethylamine (0.23 ml, 1.68 mmol) and HOBt (0.23 g, 1.68 mmol) at 0° C. After stirring at this temperature for 5 min. added 2-aminothiazole (0.168 g, 1.68 mmol) and followed by EDCI (0.332 g, 1.68 mmol). The resulting solution was stirred for 12 h. then quenched with saturated aqueous NH4Cl solution (15 mL). The aqueous phase was extracted with CH2Cl2 (3×50 mL). The organic phase was successively washed with 2% HCl (50 mL), brine (50 mL) and dried over Na2SO4. After evaporation, the residue was purified by flash chromatography (1:10 ethyl acetate:hexanes) to give 2-(4-Chloro-phenoxy)-2-methyl-N-thiazol-2-yl-propionamide (0.325 g, 78%). 1H NMR (400 MHz, CDCl3): δ 1.58 (s, 6H), 6.76 (d, J=8.8 Hz, 2H), 7.01 (d, J=3.6 Hz, 1H), 7.18 (d, J=8.8 Hz, 2H), 7.50 (d, J=3.6 Hz, 1H), MS (EI) m/z 296.9 (M+1).

Provenance & Evidence