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, 0.22 mmol), 2-(methyloxy)-4-[1-(2-methylpropyl)-4-piperidinyl]aniline (Example 160, step C) (51 mg, 0.19 mmol), and p-toluenesulfonic acid (98 mg, 0.52 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 (72 mg, 0.105 mmol, 54%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.23 (s, 1H), 9.41 (d, J=6.23 Hz, 1H), 8.52 (s, 1H), 8.33 (s, 1H), 8.24 (d, J=5.13 Hz, 1H), 8.04 (d, J=7.87 Hz, 1H), 7.80 (d, J=7.69 Hz, 1H), 7.72 (d, J=8.97 Hz, 1H), 7.57-7.65 (m, 2H), 7.43-7.49 (m, 1H), 7.35-7.43 (m, 1H), 7.16-7.22 (m, 2H), 6.99 (t, J=6.87 Hz, 1H), 6.95 (d, J=1.28 Hz, 1H), 6.78 (dd, J=8.24, 1.28 Hz, 1H), 6.48-6.54 (m, 1H), 3.82 (s, 3H), 2.90 (d, J=10.62 Hz, 2H), 2.40-2.46 (m, 1H), 1.97-2.05 (m, 2H), 1.91 (t, J=10.62 Hz, 2H), 1.65-1.76 (m, 5H), 0.84 (d, J=6.59 Hz, 6H). MS (ESI): 688 [M+H]+.
