Reaction Steps
3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-benzamide (Intermediate Example 1) (200 mg, 0.43 mmol), 5-methyl-2-(methyloxy)-4-{1-[2-(methylsulfonyl)ethyl]-4-piperidinyl}aniline (Example 163, step D) (127 mg, 0.39 mmol), and p-toluenesulfonic acid (197 mg, 1 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 1 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 10.22 (s, 1H), 9.41 (d, J=6.04 Hz, 1H), 8.47 (s, 1H), 8.32 (s, 1H), 8.24 (d, J=5.31 Hz, 1H), 8.04 (d, J=7.69 Hz, 1H), 7.80 (d, J=7.87 Hz, 1H), 7.72 (d, J=8.97 Hz, 1H), 7.59 (t, J=7.69 Hz, 1H), 7.53 (s, 1H), 7.43-7.49 (m, 1H), 7.39 (t, J=8.06 Hz, 1H), 7.19 (t, J=8.06 Hz, 2H), 6.98 (t, J=6.87 Hz, 1H), 6.88 (s, 1H), 6.51 (d, J=5.13 Hz, 1H), 3.80 (s, 3H), 3.27-3.30 (m, 2H), 3.05 (s, 3H), 2.98-3.03 (m, 2H), 2.73 (t, J=6.87 Hz, 2H), 2.59-2.68 (m, 1H), 2.18 (s, 3H), 2.03-2.14 (m, 2H), 1.64-1.74 (m, 4H). MS (ESI): 752 [M+H]+.
