Reaction Steps
A mixture of 5-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-(methyloxy)benzamide (Intermediate Example 2) (0.10 g, 0.20 mmol), 2-(ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (Example 222, Step D) (0.078 g, 0.20 mmol) and para-toluenesulfonic acid (0.093 g, 0.49 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)-5-(3-{2-[(2-(ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)-2-(methyloxy)benzamide (0.090 g, 53%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.80 (s, 1H), 9.35 (br. s., 1H), 8.36 (s, 1H), 8.24 (d, J=5.3 Hz, 1H), 8.12 (d, J=1.7 Hz, 1H), 7.75-7.83 (m, 1H), 7.71 (d, J=9.0 Hz, 1H), 7.36-7.49 (m, 3H), 7.29 (d, J=8.7 Hz, 1H), 7.15-7.25 (m, 2H), 6.88-7.01 (m, 1H), 6.67 (d, J=2.3 Hz, 1H), 6.56 (d, J=5.1 Hz, 1H), 6.49 (dd, J=8.7, 2.4 Hz, 1H), 4.07 (q, J=6.9 Hz, 2H), 4.00 (s, 3H), 3.68-3.80 (m, 2H), 3.04-3.17 (m, 4H), 2.87 (s, 3H), 2.57-2.73 (m, 6H), 2.38-2.46 (m, 1H), 1.79-1.89 (m, 2H), 1.47-1.61 (m, 2H), 1.25 (t, J=6.9 Hz, 3H). MS (M−H, ES−) 836.
