反应详情

温度

120 °C

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-(4-methyl-1-piperazinyl)propyl]aniline (56 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 hours. 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 (50 mg, 0.073 mmol, 34%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.22 (s, 1H), 9.39 (d, J=6.59 Hz, 1H), 8.50 (s, 1H), 8.31-8.34 (m, 1H), 8.25 (d, J=5.31 Hz, 1H), 8.02-8.06 (m, 1H), 7.79-7.82 (m, 1H), 7.73 (d, J=8.97 Hz, 1H), 7.56-7.64 (m, 2H), 7.45 (ddd, J=8.88, 6.78, 1.19 Hz, 1H), 7.35-7.41 (m, 1H), 7.20 (td, J=8.06, 5.13 Hz, 2H), 6.98 (t, J=6.87 Hz, 1H), 6.93 (d, J=1.47 Hz, 1H), 6.74 (dd, J=8.15, 1.56 Hz, 1H), 6.52 (d, J=5.13 Hz, 1H), 3.80 (s, 3H), 2.56 (t, J=7.60 Hz, 2H), 2.32-2.42 (m, 2H), 2.21-2.32 (m, 8H), 2.11 (s, 3H), 1.67-1.76 (m, 2H). MS (ESI): 689 [M+H]+.

1. addition1 g of silica gel was added
2. customthe pre-adsorbed solids were purified by flash chromatography