Hydrochloric Acid → HCID 59513721, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (133 mg, 0.288 mmol.) in 1 mL of EtOH/0.25 mL of DMF, N/(3-aminophenyl)acetamide (71 mg, 0.32 mmol.) and 5 uL of conc. HCl, the reaction contents were heated to 70° C. After heating for 18 h, the reaction was cooled to rt, partitioned the reaction with EtOAc and sat. aq. NaHCO3. The layers were separated, extracted the aqueous layer with EtOAc (2×10 mL), the organic layers were pooled, dried over MgSO4, filtered, reduced in vacuo onto silica. Purification via ISCO (hexanes:EtOAc) to afforded a white solid, 43 mg (26% yield). 1H NMR (400 MHz, d6-DMSO): δ 10.92 (s, 1H); 9.81 (s, 1H); 9.52 (s, 1H); 8.81 (d, J=7 Hz, 1H); 8.54 (d, J=9 Hz, 1H); 8.21 (d, J=6, 1H); 7.94 (d, J=16 Hz, 2H); 7.81 (d, J=9 Hz, 1H); 7.58-7.54 (m, 1H); 7.47-7.41 (m, 2H); 7.34 (t, J=10 Hz, 2H); 7.25-7.09 (m, 5H): 6.47 (d, J=5 Hz, 1H); 5.72 (s, 1H); 1.99 (s, 3H). HRMS calculated C32H24F2N7O2 [M+H]+ 576.1960, found 576.1945.

Provenance & Evidence