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) (200 mg, 0.4 mmol), 5-methyl-2-(methyloxy)-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}aniline (Example 163, step D) (117 mg, 0.36 mmol), and p-toluenesulfonic acid (180 mg, 0.95 mmol) were weighed into a 20 mL microwave vial. 7 mL of trifluoroethanol was added and the mixture was heated in the microwave to 150° C. for 2 h. The mixture was transferred to a 50 mL round bottom and neutralized with 2.5 mL of 0.5 N sodium methoxide. The solvent was rotovaped down. The residue was taken up in 10 mL of DCM. 2 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 (135 mg, 0.17 mmol, 43%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.74 (s, 1H), 9.39 (d, J=6.60 Hz, 1H), 8.46 (s, 1H), 8.26 (d, J=5.13 Hz, 1H), 8.05 (d, J=1.83 Hz, 1H), 7.74 (dd, J=8.62, 2.02 Hz, 1H), 7.70 (d, J=9.17 Hz, 1H), 7.56 (s, 1H), 7.41-7.49 (m, 1H), 7.37 (d, J=8.07 Hz, 1H), 7.26 (d, J=8.80 Hz, 1H), 7.19 (t, J=8.07 Hz, 2H), 6.96 (t, J=6.97 Hz, 1H), 6.89 (s, 1H), 6.58 (t, J=5.50 Hz, 1H), 4.26 (q, J=7.09 Hz, 2H), 3.79-3.82 (m, 3H), 3.26-3.36 (m, 2H), 3.06 (s, 3H), 3.02 (d, J=13.20 Hz, 4H), 2.68-2.76 (m, 2H), 2.59-2.68 (m, 1H), 2.20 (s, 3H), 2.02-2.14 (m, 2H), 1.65-1.76 (m, 2H), 1.43 (t, J=6.97 Hz, 3H). MS (ESI): 796 [M+H]+.
