Triethylamine → HCID 24960498, compound

Participants

Reaction Steps

To a solution of 2-Methyl-2-{3-[2-(4-trifluoromethyl-phenyl)-ethylamino]-phenoxy}-propionic acid (0.075 g, 0.204 mmol) in DCM (5 ml) added triethyl amine (0.034 ml, 0.24 mmol) and HOBt (0.0.037 g, 0.24 mmol) at 0° C. After stirring at this temperature for 5 min. added 2-amino-5-chlorothiazole (0.041 g, 0.285 mmol) and followed by EDCI (0.047 g, 0.244 mmol). The resulting solution was stirred for 12 h. then quenched with sat NH4Cl solution (15 ml). The aqueous phase was extracted with CH2Cl2 (3×50 ml). The organic phase were successively washed with 2% HCl (50 ml), brine (50 ml) and dried over Na2SO4. After evaporation, the residue was purified by flash chromatography (1:5 ethyl acetate:hexanes) to give N-(5-Chloro-thiazol-2-yl)-2-methyl-2-{3-[2-(4-trifluoromethyl-phenyl)-ethylamino]-phenoxy}-propionamide (0.03 g, 30%). 1H NMR (400 MHz, CDCl3): δ 1.59 (s, 6H), 2.96 (t, J=6.8 Hz, 2H), 3.39 (bs, 2H), 3.7 (bs, 1H), 6.18 (s, 1H), 6.26-6.38 (m, 2H), 7.07 (m, 1H), 7.31 (m, 2H), 7.58 (d, J=8 Hz, 2H), 10.0 (s, 1H), MS (EI) m/z: 484.1 (M+1).

Provenance & Evidence