Reaction Steps
3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-benzamide (Intermediate Example 1) (110 mg, 0.24 mmol), 2-(methyloxy)-4-[3-(1-piperidinyl)propyl]aniline (57 mg, 0.21 mol), and p-toluenesulfonic acid (109 mg, 0.57 mmol) were weighed into a 20 mL vial. 7 mL of iPrOH was added and the mixture was heated to 120° C. for 40 h. 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 (53 mg, 0.079 mmol, 37%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.23 (s, 1H), 9.40 (d, J=6.23 Hz, 1H), 8.51 (s, 1H), 8.33 (s, 1H), 8.25 (d, J=5.13 Hz, 1H), 8.04 (d, J=7.87 Hz, 1H), 7.81 (d, J=7.69 Hz, 1H), 7.73 (dd, J=8.88, 0.82 Hz, 1H), 7.56-7.64 (m, 2H), 7.45 (dd, J=8.52, 7.23 Hz, 1H), 7.35-7.42 (m, 1H), 7.19 (t, J=8.15 Hz, 2H), 6.99 (t, J=6.87 Hz, 1H), 6.93 (s, 1H), 6.74 (d, J=8.06 Hz, 1H), 6.52 (d, J=5.13 Hz, 1H), 3.81 (s, 3H), 2.56 (t, J=7.51 Hz, 2H), 2.20-2.31 (m, 6H), 1.68-1.77 (m, 2H), 1.41-1.50 (m, 4H), 1.30-1.40 (m, 2H). MS (ESI): 674 [M+H]+.
