Reaction Steps
A mixture of 5-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-(ethyloxy)benzamide (Intermediate Example 6) (0.10 g, 0.20 mmol), 2-(ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (0.076 g, 0.20 mmol) and para-toluenesulfonic acid (0.090 g, 0.47 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-(ethyloxy)-5-(3-{2-[(2-(ethyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzamide (0.072 g, 43%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.76 (s, 1H), 9.35 (br. s., 1H), 8.36 (s, 1H), 8.24 (d, J=5.2 Hz, 1H), 8.06 (d, J=1.7 Hz, 1H), 7.66-7.81 (m, 2H), 7.35-7.48 (m, 3H), 7.15-7.32 (m, 3H), 6.89-7.01 (m, 1H), 6.67 (d, J=2.3 Hz, 1H), 6.54-6.60 (m, 1H), 6.44-6.53 (m, 1H), 4.23-4.33 (m, 2H), 4.07 (q, J=6.9 Hz, 2H), 3.66-3.80 (m, 2H), 3.05-3.13 (m, 4H), 2.87 (s, 3H), 2.56-2.73 (m, 5H), 2.36-2.46 (m, 2H), 1.78-1.89 (m, 2H), 1.49-1.61 (m, 2H), 1.44 (t, J=6.9 Hz, 3H), 1.25 (t, J=7.0 Hz, 3H). MS (M−H, ES−) 850.
