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), a different batch of 2-(methyloxy)-4-(1-propyl-4-piperidinyl)aniline (48 mg, 0.19 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 24 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 (92 mg, 0.13 mmol, 68%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.77 (s, 1H), 9.37 (d, J=6.23 Hz, 1H), 8.50 (s, 1H), 8.24 (d, J=5.31 Hz, 1H), 8.10 (d, J=2.01 Hz, 1H), 7.76 (dd, J=8.61, 2.20 Hz, 1H), 7.66 (dd, J=18.77, 8.52 Hz, 2H), 7.34-7.45 (m, 2H), 7.27 (d, J=8.79 Hz, 1H), 7.17 (t, J=8.06 Hz, 2H), 6.92-6.99 (m, 2H), 6.78 (dd, J=8.06, 1.65 Hz, 1H), 6.58 (d, J=5.13 Hz, 1H), 3.97 (s, 3H), 3.81 (s, 3H), 2.87-2.97 (m, J=10.80 Hz, 2H), 2.39-2.46 (m, 1H), 2.17-2.27 (m, 2H), 1.86-1.97 (m, 2H), 1.64-1.75 (m, 4H), 1.38-1.48 (m, 2H), 0.84 (t, J=7.23 Hz, 3H). MS (ESI): 704 [M+H]+.
