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), 5-methyl-2-(methyloxy)-4-(1-propyl-4-piperidinyl)aniline (Example 157, step D) (47 mg, 0.18 mmol), and p-toluenesulfonic acid (90 mg, 0.47 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. 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 (65 mg, 0.089 mmol, 50%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.73 (s, 1H), 9.38 (d, J=6.41 Hz, 1H), 8.46 (s, 1H), 8.24 (d, J=5.31 Hz, 1H), 8.03 (d, J=2.01 Hz, 1H), 7.66-7.76 (m, 2H), 7.53 (s, 1H), 7.41-7.46 (m, 1H), 7.32-7.41 (m, 1H), 7.25 (d, J=8.61 Hz, 1H), 7.17 (t, J=8.06 Hz, 2H), 6.95 (t, J=6.68 Hz, 1H), 6.89 (s, 1H), 6.57 (d, J=5.13 Hz, 1H), 4.25 (q, J=6.90 Hz, 2H), 3.80 (s, 3H), 2.90-3.02 (m, 2H), 2.57-2.68 (m, 1H), 2.21-2.32 (m, 2H), 2.17 (s, 3H), 1.91-2.02 (m, 2H), 1.62-1.74 (m, 4H), 1.38-1.49 (m, 5H), 0.85 (t, J=7.33 Hz, 3H). MS (ESI): 732 [M+H]+.
