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-(methyloxy)-4-[1-(2-methylpropyl)-4-piperidinyl]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 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 (52 mg, 0.072 mmol, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.78 (s, 1H), 9.37 (d, J=6.59 Hz, 1H), 8.50 (s, 1H), 8.24 (d, J=5.13 Hz, 1H), 8.10 (d, J=2.01 Hz, 1H), 7.76 (dd, J=8.61, 2.20 Hz, 1H), 7.69 (d, J=8.97 Hz, 1H), 7.65 (d, J=8.06 Hz, 1H), 7.40-7.46 (m, 1H), 7.32-7.40 (m, 1H), 7.27 (d, J=8.79 Hz, 1H), 7.17 (t, J=8.06 Hz, 2H), 6.93-6.98 (m, 2H), 6.78 (dd, J=8.24, 1.47 Hz, 1H), 6.58 (d, J=5.31 Hz, 1H), 3.97 (s, 3H), 3.82 (s, 3H), 2.90 (d, J=10.07 Hz, 2H), 2.38-2.46 (m, 1H), 1.98-2.08 (m, 2H), 1.87-1.98 (m, 2H), 1.65-1.76 (m, 5H), 0.84 (d, J=6.41 Hz, 6H). MS (ESI): 718 [M+H]+.
