Reaction Steps
A mixture of 5-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-[(1-methylethyl)oxy]benzamide (Intermediate Example 7) (0.10 g, 0.19 mmol), 2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (Example 58, Step B) (0.071 g, 0.19 mmol) and para-toluenesulfonic acid (0.088 g, 0.46 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)-2-[(1-methylethyl)oxy]-5-(3-{2-[(2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzamide (0.057 g, 35%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.72 (s, 1H), 9.36 (br. s., 1H), 8.45 (s, 1H), 8.23 (d, J=5.2 Hz, 1H), 8.08 (d, J=1.9 Hz, 1H), 7.66-7.80 (m, 2H), 7.35-7.49 (m, 3H), 7.31 (d, J=8.8 Hz, 1H), 7.15-7.26 (m, 2H), 6.96 (t, J=6.6 Hz, 1H), 6.68 (d, J=2.4 Hz, 1H), 6.57 (d, J=5.1 Hz, 1H), 6.49 (dd, J=8.8, 2.3 Hz, 1H), 4.83-4.95 (m, 1H), 3.81 (s, 3H), 3.71-3.78 (m, 2H), 3.04-3.14 (m, 4H), 2.87 (s, 3H), 2.64-2.72 (m, 2H), 2.58-2.63 (m, 4H), 2.38-2.47 (m, 1H), 1.77-1.90 (m, 2H), 1.47-1.63 (m, 2H), 1.41 (d, J=6.0 Hz, 6H). MS (M−H, ES−) 850.
