Hydrochloric Acid → 1-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanone hydrochloride

Participants

Reaction Steps

1-(5-(Benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanol (prepared according to Example 19; 0.128 g, 0.375 mmol) was placed in dichloromethane (5 mL). A solution of Dess-Martin periodinane (0.167 g, 0.394 mmol) in dichloromethane (7 mL) was added and the reaction mixture was stirred at room temperature for 20 minutes. 1M NaOH and ether were added, and the layers were separated. The organic layer was washed with 1M NaOH and water, then dried, filtered, and concentrated. The residue was purified by silica gel to provide the free base, which was dissolved in dichloromethane. 2M HCl was added and the solution was concentrated to afford 1-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)ethanone hydrochloride (0.068 g, 48.3% yield). 1H NMR (DMSO-d6) δ 8.62 (d, 1H), 7.73 (m, 1H), 7.60 (m, 2H), 7.42 (m, 2H), 7.35 (m, 1H), 6.79 (s, 1H), 5.36 (s, 2H), 2.57 (s, 3H), 2.30 (s, 3H). Mass spectrum (apci) m/z=340.1 (M+H-HCl).

Provenance & Evidence