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-(2-ethyloxy)-4-(1-propyl-4-piperidinyl)aniline (Example 154, step E) (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 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. 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 (82 mg, 0.112 mmol, 63%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.73 (s, 1H), 9.32 (d, J=6.78 Hz, 1H), 8.40 (s, 1H), 8.26 (d, J=5.13 Hz, 1H), 8.05 (d, J=2.01 Hz, 1H), 7.72 (dd, J=8.70, 2.11 Hz, 1H), 7.64-7.71 (m, 2H), 7.40-7.45 (m, 1H), 7.32-7.40 (m, 1H), 7.24 (d, J=8.61 Hz, 1H), 7.17 (t, J=8.06 Hz, 2H), 6.91-6.97 (m, 2H), 6.76 (dd, J=8.24, 1.47 Hz, 1H), 6.61 (d, J=5.13 Hz, 1H), 4.24 (q, J=6.71 Hz, 2H), 4.08 (q, J=6.96 Hz, 2H), 2.93 (d, J=10.80 Hz, 2H), 2.38-2.45 (m, J=4.03 Hz, 1H), 2.16-2.27 (m, 2H), 1.91 (d, J=9.71 Hz, 2H), 1.67-1.75 (m, 2H), 1.64 (dd, J=12.00, 2.84 Hz, 2H), 1.38-1.46 (m, 5H), 1.26 (t, J=6.87 Hz, 3H), 0.84 (t, J=7.33 Hz, 3H). MS (ESI): 732 [M+H]+.
