Reaction Steps
To 5-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-(ethyloxy)benzamide (Intermediate Example 6) (0.13 g, 0.25 mmol) and 2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperidinyl}aniline (0.077 g, 0.25 mmol) in 2,2,2-trifluoroethanol (1.5 mL) was added HCl (0.13 mL, 4M in dioxane, 0.50 mmol). The reaction was heated at 180° C. for 40 min in the microwave. The reaction mixture was quenched with sodium methoxide (0.5M in MeOH) and concentrated. Purification by flash chromatography, and recrystallization with EtOH provided the title compound (0.082 g, 0.11 mmol, 43%). 1H NMR (400 MHz, DMSO-d6) δ 1.19-1.30 (m, 2H), 1.39 (t, J=6.6 Hz, 3H), 1.43-1.53 (m, 1H), 1.57-1.68 (m, 2H), 1.74 (d, J=13.9 Hz, 2H), 2.53-2.64 (m, 2H), 2.92 (s, 3H), 3.07-3.18 (m, 2H), 3.66 (d, J=11.4 Hz, 2H), 3.76 (s, 3H), 4.23 (d, J=6.2 Hz, 2H), 6.43-6.53 (m, 2H), 6.63 (s, 1H), 6.86-6.97 (m, 1H), 7.15 (t, J=7.6 Hz, 2H), 7.23 (d, J=8.4 Hz, 1H), 7.32-7.43 (m, 3H), 7.66 (d, J=9.2 Hz, 1H), 7.71 (d, J=11.5 Hz, 1H), 8.01 (s, 1H), 8.16 (d, J=5.5 Hz, 1H), 8.39 (s, 1H), 9.33 (br. s., 1H), 9.71 (s, 1H). MS (ESI) m/z=782 [M+H]+.
