Water → HCID 59276196, compound

Participants

Reaction Steps

4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzamide. A pale yellow solution of 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzonitrile (0.909 g, 2.89 mmol) in 85% phosphoric acid (15 mL) was heated at 100° C. for 2 h. Upon completion of the reaction as indicated by LCMS the reaction mixture was poured into minimum water, and made neutral with 1N sodium hydroxide (pH 6-7). The mixture was extracted with 20% isopropanol in chloroform several times. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The crude mixture was purified by silica gel chromatography using a gradient of 0-8% of saturated methanolic ammonia in chloroform to give the title compound as a pale yellow solid (0.677 g, 71% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.20 (s, 1H), 7.84 (d, 2H, J=8 Hz), 7.78-7.75 (m, 3H), 7.66 (d, 1H, J=8 Hz), 7.53 (t, 1H, J=8 Hz), 7.7.45-7.42 (m, 1H), 7.16 (br s, 1H); MS (ESI) m/z 332.16 and 334.16 [M]+ and [M+2]+

Provenance & Evidence