Reaction Steps
3-[3-(2-Chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)benzamide (Intermediate Example 1) (200 mg, 0.43 mmol), 5-methyl-2-(methyloxy)-4-{4-[2-(methyloxy)ethyl]-1-piperazinyl}aniline (Example 241, step B) (108 mg, 0.39 mmol) and p-toluenesulfonicacid (197 mg, 0.95 mmol) were weighed into a 20 mL vial. 2 mL of trifluoroethanol was added and the mixture was heated to 100° C. for 24 h. 2 mL of 2 N ammonia in MeOH was added. The solvent was rotovaped down. The residue was taken up in 3 mL of DCM. 1 g of silica gel was added. The solvent was rotovaped down and the pre-absorbed solids were purified by flash chromatography to give the title compound (125 mg, 0.18 mmol, 46%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.23 (s, 1H), 9.40 (s, 1H), 8.48 (s, 1H), 8.33 (s, 1H), 8.23 (d, J=5.13 Hz, 1H), 8.05 (d, J=7.70 Hz, 1H), 7.82 (d, J=8.07 Hz, 1H), 7.73 (d, J=9.16 Hz, 1H), 7.60 (t, J=7.70 Hz, 1H), 7.45-7.50 (m, 2H), 7.40 (tt, J=8.43, 6.23 Hz, 1H), 7.14-7.24 (m, 2H), 6.98 (t, J=6.97 Hz, 1H), 6.78 (s, 1H), 6.49 (d, J=5.13 Hz, 1H), 3.79 (s, 3H), 3.46 (t, J=5.87 Hz, 2H), 3.24 (s, 3H), 2.86 (t, J=4.58 Hz, 4H), 2.50-2.62 (m, 6H), 2.14 (s, 3H); MS (ESI): 705 [M+H]+.
