Acetyl chloride → N-(2-(2-(3-(benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)acetamide hydrochloride

Participants

Reaction Steps

Crude 4-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine (0.50 g, 1.53 mmol) was dissolved in DMF (20 mL), and triethylamine (0.854 ml, 6.13 mmol) was added, followed by the addition of acetyl chloride (0.240 g, 3.06 mmol). The reaction mixture was stirred for 2 hours, then partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried, and concentrated. The residue was dissolved in THF (10 mL) and 1N HCl in ether (2 mL) was added. The mixture was diluted in ether (15 mL) and triturated for 15 minutes, and the solids were filtered, washed with ether and hexanes, and dried to afford the title compound (0.290 g, 46.8% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 1.80 (s, 3H), 2.80 (m, 2H), 3.37 (m, 2H), 5.34 (s, 2H), 6.96 (s, 1H), 7.15 (m, 1H), 7.32-7.43 (m, 3H), 7.57-7.66 (m, 3H), 8.00 (d, 1H), 8.05 (t, 1H), 8.20 (bs, 1H), 11.35 (bs, 1H).

Provenance & Evidence