Reaction Steps
A mixture of 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)benzamide (Intermediate Example 1) (0.10 g, 0.22 mmol), 2-(ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (Example 222, Step D) (0.083 g, 0.22 mmol) and para-toluenesulfonic acid (0.099 g, 0.52 mmol) in i-PrOH (5 mL) was heated in a microwave at 175° C. for 25 min. The reaction mixture was concentrated onto silica gel and purified by flash chromatography. Recrystallization from DCM and diethyl ether afforded N-(2,6-difluorophenyl)-3-(3-{2-[(2-(ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzamide (0.110 g, 63%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.25 (s, 1H), 9.39 (br. s., 1H), 8.38 (s, 1H), 8.35 (s, 1H), 8.24 (d, J=5.2 Hz, 1H), 8.06 (d, J=7.9 Hz, 1H), 7.82 (d, J=7.8 Hz, 1H), 7.74 (d, J=9.0 Hz, 1H), 7.62 (t, J=7.7 Hz, 1H), 7.36-7.52 (m, 3H), 7.16-7.26 (m, 2H), 6.94-7.02 (m, 1H), 6.67 (d, J=2.2 Hz, 1H), 6.45-6.54 (m, 2H), 4.07 (q, J=6.9 Hz, 2H), 3.66-3.79 (m, 2H), 3.04-3.15 (m, 4H), 2.87 (s, 3H), 2.57-2.72 (m, 6H), 2.36-2.47 (m, 1H), 1.78-1.91 (m, 2H), 1.45-1.62 (m, 2H), 1.25 (t, J=7.0 Hz, 3H). MS (M−H, ES−) 806.
