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-(2-ethyloxy)-4-(1-propyl-4-piperidinyl)aniline (Example 154, step E) (51 mg, 0.19 mmol), and p-toluenesulfonic acid (98 mg, 0.51 mmol) were weighed into a 20 mL vial. 7 mL of iPrOH was added and the mixture was heated to 130° 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 (32 mg, 0.112 mmol, 24%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.23 (s, 1H), 9.36 (d, J=6.78 Hz, 1H), 8.41 (s, 1H), 8.33 (s, 1H), 8.27 (d, J=5.31 Hz, 1H), 8.04 (d, J=7.87 Hz, 1H), 7.80 (d, J=7.87 Hz, 1H), 7.73 (d, J=8.97 Hz, 1H), 7.65 (d, J=8.06 Hz, 1H), 7.59 (t, J=7.78 Hz, 1H), 7.42-7.49 (m, 1H), 7.34-7.42 (m, 1H), 7.19 (t, J=8.06 Hz, 2H), 6.98 (t, J=6.78 Hz, 1H), 6.93 (s, 1H), 6.76 (d, J=8.42 Hz, 1H), 6.55 (d, J=5.13 Hz, 1H), 4.08 (q, J=6.90 Hz, 2H), 2.88-3.00 (m, 2H), 2.38-2.45 (m, 1H), 2.19-2.30 (m, 2H), 1.87-1.99 (m, 2H), 1.63-1.75 (m, 4H), 1.39-1.49 (m, 2H), 1.26 (t, J=6.96 Hz, 3H), 0.84 (t, J=7.23 Hz, 3H). MS (ESI): 688 [M+H]+.
