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) (2.9 g, 5.7 mmol) and (5-methyl-2-(ethyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1-piperazinyl}phenyl)amine (2.0 g, 5.7 mmol) in trifluoroethanol (100 mL) was added p-toluene sulfonic acid (2.2 g, 11 mmol), and the vial was sealed and heated to 80° C. overnight. The reaction was then cooled to rt and excess 0.5 M NaOMe in MeOH was added. The solution was transferred to a roundbottom flask and silica was added. The solvent was removed on a rotovap and the product purified on a 120 g ISCO column. Desired fractions were combined and rotovaped down. The resulting foam was dissolved in DCM and ether was added to provide the title compound 2.5 g, 3.1 mmol, 54% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.71 (s, 1H), 9.33 (d, J=6.7 Hz, 1H), 8.32 (s, 1H), 8.23 (d, J=5.4 Hz, 1H), 8.02 (s, 1H), 7.73-7.70 (m, 1H), 7.67 (d, J=9.0 Hz, 1H), 7.53 (s, 1H), 7.43-7.31 (m, 2H), 7.23 (d, J=8.6 Hz, 1H), 7.16 (t, J=8.0 Hz, 2H), 6.92 (t, J=6.6 Hz, 1H), 6.71 (s, 1H), 6.56 (d, J=5.1 Hz, 1H), 4.23 (q, J=7.2 Hz, 2H), 4.04 (q, J=7.0 Hz, 2H), 3.33-3.25 (m, 2H), 3.03 (s, 3H), 2.84-2.78 (m, 4H), 2.74 (t, J=6.6 Hz, 2H), 2.63-2.46 (m, 4H), 2.11 (s, 3H), 1.40 (t, J=6.8 Hz, 3H), 1.23 (t, J=7.0 Hz, 3H). MS (ESI) m/z=811 [M+H]+.
