3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-benzamide → N-(2,6-difluorophenyl)-3-(3-(2-(3-(2-(dimethylamino)ethoxy)phenylamino)pyrimidin-4-yl)imidazo[1,2-a]pyridin-2-yl)benzamide

Participants

Reaction Conditions

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) (0.150 g, 0.325 mmol) and 3-{[2-(dimethylamino)ethyl]oxy}aniline hydrochloride (PCT Publication No. WO2004/087652) (0.63 g, 0.29 mmol) were taken up in iPrOH (3 mL) and concentrated HCl (5 drops) was added. The vial was sealed and heated in the microwave at 180° C. for 15 min. The crude product was adsorbed onto silica gel and flash chromatographed to give the title compound (0.047 g, 26%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.22 (s, 1H), 9.75 (s, 1H), 9.51 (d, J=6.6 Hz, 1H), 8.26-8.47 (m, 2H), 8.03 (d, J=7.7 Hz, 1H), 7.84 (d, J=7.7 Hz, 1H), 7.76 (d, J=9.0 Hz, 1H), 7.59 (t, J=7.8 Hz, 1H), 7.44-7.54 (m, 2H), 7.31-7.44 (m, 1H), 7.11-7.29 (m, 4H), 7.08 (t, J=6.6 Hz, 1H), 6.62 (d, J=5.3 Hz, 1H), 6.53 (dd, J=8.2, 1.6 Hz, 1H), 3.94 (t, J=5.8 Hz, 2H), 2.55 (t, J=5.7 Hz, 2H), 2.14 (s, 6H). MS (M+H, ES+) 606.

Provenance & Evidence