Reaction Steps
To 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-benzamide (Intermediate Example 1) (0.11 g, 0.25 mmol) and 2-(methyloxy)-4-[4-(1-piperidinylmethyl)-1-piperidinyl]aniline (0.076 g, 0.25 mmol) in trifluoroethanol (1.5 mL) was added HCl (0.13 mL, 4M in dioxane, 0.50 mmol). The reaction was heated at 170° C. for 80 min in the microwave. When complete by MS, the reaction mixture was quenched with sodium methoxide (0.5M in MeOH) and concentrated. Purification by flash chromatography, followed by prep-HPLC, and recrystallization with DCM/hexanes provided the title compound (0.082 g, 0.11 mmol, 46%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.14-1.26 (m, 2H), 1.36 (br. s., 2H), 1.43-1.53 (m, 4H), 1.63 (br. s., 1H), 1.77 (d, J=11.7 Hz, 2H), 2.09 (d, J=7.0 Hz, 2H), 2.27 (s, 4H), 2.63 (t, J=12.1 Hz, 2H), 3.67 (d, J=11.4 Hz, 2H), 3.78 (s, 3H), 6.40-6.51 (m, 2H), 6.65 (d, J=2.2 Hz, 1H), 6.97 (t, J=7.0 Hz, 1H), 7.20 (t, J=8.1 Hz, 2H), 7.35-7.42 (m, 2H), 7.44-7.48 (m, 1H), 7.60 (t, J=7.7 Hz, 1H), 7.72 (d, J=9.2 Hz, 1H), 7.81 (d, J=7.7 Hz, 1H), 8.05 (d, J=8.1 Hz, 1H), 8.19 (d, J=5.1 Hz, 1H), 8.33 (s, 1H), 8.46 (s, 1H), 9.40 (br. s., 1H), 10.24 (s, 1H). MS (M+H, ES+) 729.
