Reaction Steps
In a 5 mL microwave vial with septum cap, 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-benzamide (Intermediate Example 1) (0.200 g, 0.433 mmol), 4-(1,4′-bipiperidin-1′-yl)-2-(propyloxy)aniline (0.137 g, 0.433 mmol) were taken up in iPrOH (3 mL) and concentrated HCl (3 drops) was added. The vial was sealed and heated in the microwave at 165° C. for 30 min. The reaction was cooled to rt, neutralized with 7N ammonia in MeOH, adsorbed onto silica gel, and flash chromatographed. Product was then triturated with diethyl ether to give the title compound (0.184 g, 58%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.20 (s, 1H), 9.18-9.41 (m, 1H), 8.24-8.47 (m, 2H), 8.18 (d, J=4.9 Hz, 1H), 8.02 (d, J=7.5 Hz, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.57 (t, J=7.6 Hz, 1H), 7.26-7.48 (m, 3H), 7.17 (t, J=8.1 Hz, 2H), 6.83-7.01 (m, 1H), 6.63 (br. s., 1H), 6.43 (d, J=5.1 Hz, 2H), 3.91 (t, J=6.0 Hz, 2H), 3.69 (d, J=11.4 Hz, 2H), 2.60 (t, J=11.6 Hz, 2H), 2.36-2.52 (m, 4H), 2.22-2.36 (m, 1H), 1.75 (d, J=11.0 Hz, 2H), 1.14-1.66 (m, 10H), 0.66-0.88 (m, 3H). MS (M+H) 743.
