Chloroacetone → N-(3-(benzyloxy)-5-(2-chlorophenoxy)pyridin-2-yl)-4-methylthiazol-2-amine hydrochloride

Participants

Reaction Steps

A mixture of 1-(3-(benzyloxy)-5-(2-chlorophenoxy)pyridin-2-yl)thiourea (0.280 g, 0.660 mmol), 1-chloropropan-2-one (0.0733 g, 0.792 mmol), triethylamine (0.161 ml, 1.16 mmol), and ethanol (10 mL) was heated at reflux overnight. The reaction mixture was cooled and partitioned between ethyl acetate:ether (1:1) and water. The organic layer was washed with water, brine, dried, and concentrated. The residue was purified via MPLC (Biotage) eluting with 3:1 hexane:ethyl acetate to afford a free base of the title compound as a light yellow oil. The oil was dissolved in ether (6 mL), and 1M HCl in ether (2 mL) was added. The mixture was sonicated to break up the white solid. Hexanes (5 mL) were added, and the mixture was sonicated and filtered. The solids were washed with hexanes and dried to provide 3-(benzyloxy)-5-(2-chlorophenoxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (0.215 g, 70.7% yield) as a white powder. 1H NMR (DMSO-d6) δ 2.31 (s, 3H), 5.33 (s, 2H), 6.82 (s, 1H), 7.01 (d, 1H), 7.22 (t, 1H), 7.32-7.43 (m, 5H), 7.51-7.62 (m, 5H), 7.67 (d, 1H).

Provenance & Evidence