4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 57898961, compound

Participants

Reaction Steps

A solution of ethyl 2-(2-(4-(naphthalen-1-yloxy)pyridin-2-ylamino)thiazol-4-yl)acetate (prepared from 2-chloro-4-(naphthalen-1-yloxy)pyridine (1.18 g, 4.61 mmol) and ethyl 2-(2-aminothiazol-4-yl)acetate according to the method of example 1 step B; 0.370 g, 0.913 mmol) in THF (4 ml) was added to a 1M solution of lithium aluminum hydride in THF (5 mL) at 0° C. The reaction mixture was stirred at ambient temperature for one hour, then cooled in an ice bath and quenched carefully with an excess of sodium sulfate decahydrate and stirred overnight. The reaction mixture was filtered, the solids were washed with THF several times, and the combined filtrate was concentrated. The crude material was purified via MPLC, eluting first with 1:1 hexane:ethyl acetate, followed by ethyl acetate. The component which eluted with ethyl acetate was concentrated and triturated with hexanes:dichloromethane (4:1, 15 mL), filtered, washed with hexanes, and dried to afford the title compound (0.125 g, 37.7% yield). 1H NMR (d6-DMSO) δ 2.67 (t, 2H), 3.63 (q, 2H), 4.57 (t, 1H), 6.51 (s, 1H), 6.57 (m, 214), 7.36 (d, 1H), 7.55-7.63 (m, 3H), 7.85 (d, 1H), 7.92 (d, 1H), 8.05 (d, 1H), 8.17 (d, 1H), 10.97 (s, 1H).

Provenance & Evidence