To 5-[3-(2-Chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-(methyloxy)benzamide (Intermediate Example 2) (0.241 g, 0.490 mmol) and 4-{(3S)-3-(1-methylethyl)-4-[2-(methylsulfonyl)ethyl]-1-piperazinyl}-2-(methyloxy)aniline (0.174 g, 0.489 mmol) were dissolved in 5 mL of trifluoroethanol with stirring in a pressure vessel. Hydrogen chloride (0.49 mL, 4N in dioxane, 2.0 mmol) was added, and the vessel was sealed. The reaction was heated to 80° C. for 3 days and subsequently cooled to rt. The reaction was poured into 10 mL of 7N NH3 in MeOH and concentrated onto silica gel. The compound was purified by flash chromatography, and the fractions containing the desired compound were concentrated in vacuo. The material was triturated with diethyl ether, filtered, and washed with diethyl ether. The solid was collected to afford the title compound (0.191 g, 0.236 mmol, 48%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.75 (s, 1H), 9.33 (br. s., 1H), 8.42 (s, 1H), 8.17 (d, J=5.1 Hz, 1H), 8.03-8.09 (m, 1H), 7.70-7.78 (m, 1H), 7.66 (d, J=9.0 Hz, 1H), 7.29-7.43 (m, 3H), 7.25 (d, J=8.8 Hz, 1H), 7.10-7.19 (m, 2H), 6.87-6.95 (m, 1H), 6.61 (s, 1H), 6.43-6.52 (m, 2H), 3.95 (s, 3H), 3.77 (s, 3H), 3.43-3.51 (m, 1H), 3.30-3.41 (m, 2H), 3.27 (s, 3H), 2.99 (s, 3H), 2.91-2.98 (m, 1H), 2.68-2.85 (m, 2H), 2.51-2.60 (m, 1H), 2.22-2.30 (m, 1H), 2.05-2.16 (m, 1H), 0.96 (d, J=6.8 Hz, 3H), 0.87 (d, J=7.0 Hz, 3H). MS (M+H, ES+) 811.
