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) (100 mg, 0.2 mmol), 2-(ethyloxy)-4-(4-propyl-1-piperazinyl)aniline (Example 151, step B) (47 mg, 0.18 mmol), and p-toluenesulfonic acid (90 mg, 0.48 mmol) were weighed into a 20 mL vial. 7 mL of iPrOH was added and the mixture was heated to 130° C. for 72 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 (67 mg, 0.091 mmol, 52%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.73 (s, 1H), 9.33 (s, 1H), 8.35 (s, 1H), 8.21 (d, J=5.13 Hz, 1H), 8.04 (d, J=2.01 Hz, 1H), 7.72 (dd, J=8.61, 2.01 Hz, 1H), 7.68 (d, J=8.97 Hz, 1H), 7.34-7.45 (m, 3H), 7.24 (d, J=8.61 Hz, 1H), 7.18 (t, J=8.06 Hz, 2H), 6.92 (t, J=6.59 Hz, 1H), 6.64 (d, J=2.20 Hz, 1H), 6.53 (d, J=5.13 Hz, 1H), 6.45 (dd, J=8.70, 2.47 Hz, 1H), 4.24 (q, J=6.78 Hz, 2H), 4.04 (q, J=6.96 Hz, 2H), 3.06-3.16 (m, 4H), 2.43-2.52 (m, 4H), 2.25 (t, J=6.96 Hz, 2H), 1.39-1.48 (m, 5H), 1.22 (t, J=6.96 Hz, 3H), 0.85 (t, J=7.33 Hz, 3H). MS (ESI): 733 [M+H]+.
