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) (110 mg, 0.22 mmol), 22-(methyloxy)-4-[3-(4-methyl-1-piperazinyl) propyl]aniline (Example 141, step B) (53 mg, 0.20 mol), and p-toluenesulfonic acid (102 mg, 0.54 mmol) were weighed into a 20 mL vial. 7 mL of iPrOH was added and the mixture was heated to 120° C. for 40 h. The mixture was transferred to a 50 mL round bottom and neutralized with 2 mL of 0.5 N sodium methoxide. The solvent was rotovaped down. The residue was taken up in 10 mL of DCM. 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 (50 mg, 0.07 mmol, 35%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.77 (s, 1H), 9.36 (d, J=6.78 Hz, 1H), 8.49 (s, 1H), 8.25 (d, J=5.13 Hz, 1H), 8.10 (d, J=2.20 Hz, 1H), 7.76 (dd, J=8.61, 2.20 Hz, 1H), 7.67-7.73 (m, 1H), 7.63 (d, J=7.87 Hz, 1H), 7.40-7.45 (m, 1H), 7.33-7.40 (m, 1H), 7.27 (d, J=8.79 Hz, 1H), 7.13-7.21 (m, 2H), 6.94-6.98 (m, 1H), 6.93 (d, J=1.65 Hz, 1H), 6.74 (dd, J=8.06, 1.65 Hz, 1H), 6.58 (d, J=5.31 Hz, 1H), 3.97 (s, 3H), 3.80 (s, 3H), 2.56 (t, J=7.60 Hz, 2H), 2.32-2.42 (m, 2H), 2.20-2.32 (m, 8H), 2.09-2.13 (m, 3H), 1.67-1.76 (m, 2H). MS (ESI): 719 [M+H]+.
