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-(2-ethyloxy)-4-(1-propyl-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 (75 mg, 0.104 mmol, 57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.77 (s, 1H), 9.33 (d, J=6.78 Hz, 1H), 8.41 (s, 1H), 8.26 (d, J=5.13 Hz, 1H), 8.10 (d, J=1.83 Hz, 1H), 7.76 (dd, J=8.52, 1.92 Hz, 1H), 7.64-7.72 (m, 2H), 7.40-7.46 (m, 1H), 7.33-7.40 (m, 1H), 7.26 (d, J=8.61 Hz, 1H), 7.17 (t, J=8.06 Hz, 2H), 6.90-6.97 (m, 2H), 6.77 (d, J=8.24 Hz, 1H), 6.61 (d, J=5.31 Hz, 1H), 4.08 (q, J=6.96 Hz, 2H), 3.96 (s, 3H), 2.90-3.01 (m, 2H), 2.39-2.45 (m, 1H), 2.20-2.32 (m, 2H), 1.90-2.02 (m, 2H), 1.70-1.79 (m, 2H), 1.58-1.70 (m, 2H), 1.39-1.50 (m, 2H), 1.27 (t, J=6.96 Hz, 3H), 0.84 (t, J=7.33 Hz, 3H). MS (ESI): 718 [M+H]+.
