Reaction Steps
5-[3-(2-Chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-(methyloxy)benzamide (Intermediate Example 2) (100 mg, 0.2 mmol), 2-(methyloxy)-4-{4-[2-(methyloxy)ethyl]-1-piperazinyl}aniline (Example 238, step A) (48 mg, 0.18 mmol), and p-toluenesulfonicacid (93 mg, 0.49 mmol) were weighed into a 20 mL vial. 1 mL of trifluoroethanol was added and the mixture was heated to 100° C. for 72 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 (85 mg, 0.12 mmol, 64%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.78 (s, 1H), 9.36 (s, 1H), 8.45 (s, 1H), 8.20 (d, J=5.50 Hz, 1H), 8.10 (d, J=2.20 Hz, 1H), 7.77 (dd, J=8.80, 2.20 Hz, 1H), 7.69 (d, J=9.17 Hz, 1H), 7.34-7.46 (m, 3H), 7.28 (d, J=8.80 Hz, 1H), 7.18 (t, J=8.07 Hz, 2H), 6.90-6.98 (m, 1H), 6.67 (d, J=2.57 Hz, 1H), 6.52 (d, J=5.13 Hz, 1H), 6.45-6.51 (m, 1H), 3.98 (s, 3H), 3.79 (s, 3H), 3.46 (t, J=5.87 Hz, 2H), 3.24 (s, 3H), 3.10-3.17 (m, 4H), 2.53-2.58 (m, 4H), 2.51 (t, J=5.87 Hz, 2H); MS (ESI): 721 [M+H]+.
