Hydrogen Peroxide → HCID 178513661, compound

Participants

Reaction Steps

tert-Butyl cis-4-(2-(4-carbamoylphenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)cyclohexylcarbamate. To a pale yellow solution of tert-butyl cis-4-(2-(4-cyanophenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)cyclohexylcarbamate (0.078 g, 0.174 mmol) in ethanol (10 mL) (heated with a heat gun to get the starting material in solution) was added 3 N sodium carbonate (4 mL) and 30% w/w hydrogen peroxide (4 mL) at room temperature. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction as indicated by LCMS, the reaction mixture was poured into brine, and extracted with ethyl acetate several times. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated. The crude mixture was purified by column chromatography (eluting with 0-10% saturated methanolic ammonia in chloroform) to give the title compound as a pale pink solid (0.066 g, 81% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 9.86 (s, 1H), 7.84 (d, 2H, J=8 Hz), 7.76 (d, 3H, J=8 Hz), 7.44 (t, 1H, J=8 Hz), 7.12 (s, 1H), 6.78 (d, 1H, J=8 Hz), 6.22 (d, 1H, J=8 Hz), 5.96 (d, 1H, J=8 Hz), 3.73-3.65 (m, 1H), 3.58-3.51 (m, 1H), 1.91-1.82 (m, 2H), 1.81-1.73 (m, 2H), 1.69-1.58 (m, 4H), 1.40 (s, 9H); MS (ESI) m/z 466.55 [M+1]+.

Provenance & Evidence