Reaction Steps
5-[3-(2-Chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-(ethyloxy)benzamide (Intermediate Example 6) (200 mg, 0.4 mmol), 5-methyl-2-(methyloxy)-4-{4-[2-(methyloxy)ethyl]-1-piperazinyl}aniline (99 mg, 0.36 mmol) and p-toluenesulfonicacid (180 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 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 (150 mg, 0.2 mmol, 56%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.74 (s, 1H), 9.36 (s, 1H), 8.46 (s, 1H), 8.23 (d, J=5.13 Hz, 1H), 8.04 (d, J=1.83 Hz, 1H), 7.74 (dd, J=8.43, 2.20 Hz, 1H), 7.69 (d, J=9.17 Hz, 1H), 7.49 (s, 1H), 7.41-7.47 (m, 1H), 7.34-7.41 (m, 1H), 7.26 (d, J=8.43 Hz, 1H), 7.19 (t, J=8.07 Hz, 2H), 6.95 (t, J=6.97 Hz, 1H), 6.77 (s, 1H), 6.55 (d, J=5.13 Hz, 1H), 4.26 (q, J=6.84 Hz, 2H), 3.80 (s, 3H), 3.42-3.48 (m, 2H), 3.24 (s, 3H), 2.86 (t, J=4.40 Hz, 4H), 2.50-2.61 (m, 6H), 2.14 (s, 3H), 1.43 (t, J=6.97 Hz, 3H); MS (ESI): 749 [M+H]+.
