Ammonium Chloride → HCID 25050519, compound

Participants

Reaction Steps

Lithium boranate (7 mg, 322 μmol) was added to a solution of Ethyl 2-(2-(3-(3,4-dichlorobenzyl)ureido)thiazol-4-yl)acetate (Example 35) (58 mg, 150 μmol) in dry THF (4 ml) at 0° C. The reaction mixture was stirred for 3 hours at this temperature and then allowed to warm to ambient temperature overnight. Then, saturated aqueous ammonium chloride solution (3 ml) was added and the mixture was stirred for 2 hours. The salts were dissolved by addition of a few drops of water, and the mixture was extracted several times with ethyl acetate. The combined organic layers were partitioned with brine and then dried over sodium sulfate, filtered, and volatiles removed in vacuo. The crude material was purified by column chromatography (silica gel, acetone/ethyl acetate, 1:20, 1:15, 1:10), yielding the title compound in 60% (32 mg, 92 mmol). 1H NMR (300 MHz, CD3OD) δ 2.80 (t, 2H), 3.81 (t, 2H), 4.40 (s, 2H), 6.60 (s, 1H), 7.24 (dd, 1H), 7.42-7.48 (m, 2H). MS (ES+): M/Z 346 and 348 (M+H).

Provenance & Evidence