Reaction Steps
3-[3-(2-Chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)benzamide (Intermediate Example 1) (100 mg, 0.22 mmol), 2-(methyloxy)-4-{4-[2-(methyloxy)ethyl]-1-piperazinyl}aniline (Example 238, step A) (51 mg, 0.194 mmol), and p-toluenesulfonicacid (99 mg, 0.52 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 (72 mg, 0.104 mmol, 53%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.24 (s, 1H), 9.40 (s, 1H), 8.47 (s, 1H), 8.33 (s, 1H), 8.20 (d, J=5.50 Hz, 1H), 8.05 (d, J=7.70 Hz, 1H), 7.81 (d, J=8.07 Hz, 1H), 7.72 (d, J=8.80 Hz, 1H), 7.61 (t, J=7.88 Hz, 1H), 7.43-7.49 (m, 1H), 7.35-7.43 (m, 2H), 7.17-7.24 (m, 2H), 6.97 (t, J=6.97 Hz, 1H), 6.67 (d, J=2.20 Hz, 1H), 6.46 (d, J=5.50 Hz, 2H), 3.79 (s, 3H), 3.46 (t, J=5.68 Hz, 2H), 3.24 (s, 3H), 3.09-3.16 (m, 4H), 2.53-2.58 (m, 4H), 2.51 (t, J=5.87 Hz, 2H); MS (ESI): 691 [M+H]+.
