p-Toluenesulfonic acid → N-(2,6-difluorophenyl)-5-{3-[2-({2-(ethyloxy)-4-[2-(4-methyl-1-piperazinyl)ethyl]-phenyl}amino)-4-pyrimidinyl]imidazo[1,2-a]pyridin-2-yl}-2-(methyloxy)benzamide

Participants

Reaction Conditions

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) (100 mg, 0.2 mmol), 2-(ethyloxy)-4-[2-(4-methyl-1-piperazinyl)ethyl]aniline (44 mg, 0.17 mmol), and p-toluenesulfonic acid (93 mg, 0.49 mmol) were weighed into a 20 mL microwave vial. 7 mL of iPrOH was added and the mixture was heated to 130° C. for 72 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 (85 mg, 0.118 mmol, 71%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.77 (s, 1H), 9.32 (d, J=6.96 Hz, 1H), 8.39 (s, 1H), 8.27 (d, J=5.31 Hz, 1H), 8.11 (s, 1H), 7.76 (d, J=8.42 Hz, 1H), 7.68 (dd, J=11.81, 8.52 Hz, 2H), 7.33-7.45 (m, 2H), 7.26 (d, J=8.79 Hz, 1H), 7.17 (t, J=7.97 Hz, 2H), 6.88-6.99 (m, 2H), 6.74 (d, J=8.06 Hz, 1H), 6.61 (d, J=5.13 Hz, 1H), 4.06 (q, J=6.96 Hz, 2H), 3.97 (s, 3H), 2.62-2.72 (m, 2H), 2.19-2.57 (m, 10H), 2.11 (s, 3H), 1.27 (t, J=7.05 Hz, 3H). MS (ESI): 719 [M+H]+.

Provenance & Evidence