Reaction Steps
3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-benzamide (Intermediate Example 1) (100 mg, 0.2 mmol), a different batch of 2-(methyloxy)-4-(1-propyl-4-piperidinyl)aniline (Example 137, step D) (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 hours. 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 (104 mg, 0.154 mmol, 80%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.23 (s, 1H), 9.41 (d, J=6.59 Hz, 1H), 8.52 (s, 1H), 8.32 (s, 1H), 8.24 (d, J=5.31 Hz, 1H), 8.04 (d, J=7.87 Hz, 1H), 7.80 (d, J=7.87 Hz, 1H), 7.72 (d, J=8.97 Hz, 1H), 7.60 (q, J=7.63 Hz, 2H), 7.44-7.49 (m, 1H), 7.35-7.42 (m, 1H), 7.19 (t, J=8.15 Hz, 2H), 6.99 (t, J=6.96 Hz, 1H), 6.96 (d, J=1.47 Hz, 1H), 6.78 (dd, J=8.24, 1.65 Hz, 1H), 6.52 (d, J=5.31 Hz, 1H), 3.81 (s, 3H), 2.89-2.99 (m, J=8.79 Hz, 2H), 2.39-2.46 (m, 1H), 2.18-2.28 (m, 2H), 1.87-1.98 (m, 2H), 1.64-1.76 (m, 4H), 1.39-1.48 (m, 2H), 0.84 (t, J=7.33 Hz, 3H). MS (ESI): 674 [M+H]+.
