Hydrochloric Acid → 2,6-Difluoro-N-{3-[3-(2-{[4-(4-morpholinyl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}benzamide

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 (100 mg, 0.216 mmol.) in 1 mL of EtOH, added 4-(4-morpholinyl)aniline (38 mg, 0.216 mmol.) and 5 μL of conc. HCl. The reaction contents were heated to 80° C. After heating for 18 h, the reaction was cooled to rt and partitioned between 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. Purified via ISCO chromatography (hexanes:EtOAc) to afford the desired compound as a yellow solid, 56 mg, 43% yield. 1H NMR (400 MHz, CD3OD): δ 8.61 (d, J=7 Hz, 1H); 8.40 (d, J=9 Hz, 1H); 8.14 (d, J=5 Hz, 1H); 7.98 (bs, 1H); 7.86 (d, J=7H, 1H); 7.56-7.48 (m, 3H); 7.48-7.37 (m, 3H); 7.12-7.05 (m, 3H); 6.92 (d, J=9 Hz, 2H) 6.58 (d, J=5 Hz, 1H); 3.85-3.83 (m, 4H); 3.11-3.09 (m 4H). HRMS calculated C34H28F2N7O2 [M+H]+ 604.2273, found 604.2271.

Provenance & Evidence