Pyridine → 1-(4-(5-(5-Bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

1-acetyl-N-(methylsulfonyloxy)piperidine-4-carbimidoyl chloride (2.27 g, 8.03 mmol), pyridine (1.95 mL, 24.1 mmol) and sodium thiocyanate (0.651 g, 8.03 mmol) were dissolved in acetonitrile (45 mL). The solution was heated to 40° C. for 40 minutes. 5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-amine (1.50 g, 5.35 mmol) was added and the reaction was heated at 60° C. overnight. The solution was cooled to 0° C., filtered and the solid was dried to give 1-(4-(5-(5-bromo-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (2.63 g, 5.37 mmol, 100% yield) as a white solid. 1H NMR (CDCl3) δ 1.78-1.97 (m, 2H), 2.01-2.20 (m, 2H), 2.12 (s, 3H), 2.51 (s, 3H), 2.86 (t, 1H), 3.05-3.11 (m, 1H), 3.24 (t, 1H), 3.90 (d, 1H), 4.57 (d, 1H), 6.97 (d, 1H), 7.24-7.37 (m, 2H), 8.23 (d, 1H), 8.50 (d, 1H), 9.10 (bs, 1H).

Provenance & Evidence