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-(ethyloxy)-4-(4-propyl-1-piperazinyl)aniline (Example 151, step B) (51 mg, 0.19 mmol), and p-toluenesulfonic acid (98 mg, 0.52 mmol) were weighed into a 20 mL vial. 7 mL of iPrOH was added and the mixture was heated to 120° C. for 48 h. The mixture was transferred to a 50 mL round bottom and neutralized with 3 mL of 0.5 N sodium methoxide 1 g of silica gel was added. The solvent was rotovaped down and the pre-adsorbed solids were purified by flash chromatography to give the title compound (64 mg, 0.093 mmol, 47%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.23 (s, 1H), 9.35 (s, 1H), 8.34 (d, J=15.93 Hz, 2H), 8.21 (d, J=5.31 Hz, 1H), 8.03 (d, J=7.87 Hz, 1H), 7.80 (d, J=7.69 Hz, 1H), 7.71 (d, J=8.97 Hz, 1H), 7.59 (t, J=7.78 Hz, 1H), 7.35-7.46 (m, 3H), 7.16-7.22 (m, 2H), 6.95 (t, J=6.78 Hz, 1H), 6.64 (d, J=2.20 Hz, 1H), 6.43-6.48 (m, 2H), 4.04 (q, J=6.96 Hz, 2H), 3.07-3.13 (m, 4H), 2.42-2.51 (m, 4H), 2.25 (t, J=7.33 Hz, 2H), 1.40-1.48 (m, 2H), 1.22 (t, J=6.96 Hz, 3H), 0.85 (t, J=7.33 Hz, 3H). MS (ESI): 689 [M+H]+.
