Potassium Carbonate → HCID 59291610, compound

Participants

Reaction Steps

A mixture of 2-(6-(3-(1-acetyl-4-methylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)ethyl acetate (89 mg, 0.164 mmol) and potassium carbonate (113 mg, 0.820 mmol) in ethanol (25 mL) was heated at reflux for 2 hr. The reaction was filtered and concentrated, and the residue was purified by reverse phase with 0.1% TFA buffer. The purified fractions were poured into saturated sodium bicarbonate and extracted with methylene chloride to afford 1-(4-(5-(5-(2-hydroxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-4-methylpiperidin-1-yl)ethanone (36.8 mg, 0.0735 mmol, 44.8% yield). 1H NMR (d6-DMSO) δ 12.18 (s, 1H), 8.28 (d, 1H), 8.26 (dd, 1H), 7.44 (d, 1H), 7.25-7.15 (m, 2H), (4.89 (m, 1H), 3.89 (m, 1H), 3.60 (m, 1H), 3.52 (m, 2H), 3.18 (t, 1H), 3.00-2.88 (m, 3H), 2.53 (m, 3H), 2.31 (m, 2H), 1.97 (s, 3H), 1.62-1.40 (m, 2H), 1.26 (s, 3H).

Provenance & Evidence