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-(ethyloxy)-4-(4-propyl-1-piperazinyl)aniline (48 mg, 0.18 mmol), and p-toluenesulfonic acid (93 mg, 0.49 mmol) were weighed into a 20 mL vial. 7 mL of iPrOH was added and the mixture was heated to 130° 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 (52 mg, 0.072 mmol, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.78 (s, 1H), 9.32 (s, 1H), 8.35 (s, 1H), 8.21 (d, J=5.31 Hz, 1H), 8.09 (d, J=2.01 Hz, 1H), 7.76 (dd, J=8.61, 2.01 Hz, 1H), 7.68 (d, J=8.97 Hz, 1H), 7.35-7.45 (m, 3H), 7.26 (d, J=8.79 Hz, 1H), 7.17 (t, J=8.06 Hz, 2H), 6.92 (t, J=6.87 Hz, 1H), 6.64 (d, J=2.20 Hz, 1H), 6.53 (d, J=5.31 Hz, 1H), 6.46 (dd, J=8.79, 2.38 Hz, 1H), 4.04 (q, J=6.96 Hz, 2H), 3.97 (s, 3H), 3.07-3.13 (m, 4H), 2.43-2.51 (m, 4H), 2.26 (t, J=7.23 Hz, 2H), 1.40-1.50 (m, J=7.36, 7.36, 7.36, 7.36, 7.36 Hz, 2H), 1.22 (t, J=6.96 Hz, 3H), 0.85 (t, J=7.42 Hz, 3H). MS (ESI): 719 [M+H]+.
