p-Toluenesulfonic acid → N-(2,6-difluorophenyl)-3-[3-(2-{[2-(methyloxy)-4-(4-{4-[2-(methylsulfonyl)ethyl]-1-piperazinyl}-1-piperidinyl)phenyl]amino}-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-benzamide (Intermediate Example 1) (0.70 g, 1.52 mmol), 2-(methyloxy)-4-(4-{4-[2-(methylsulfonyl)ethyl]-1-piperazinyl}-1-piperidinyl)aniline (0.60 g, 1.52 mmol), p-toluenesulfonic acid (0.69 g, 3.64 mmol) and iPrOH (15 mL) were heated in the microwave at 175° C. for 25 min. LCMS indicated the reaction had proceeded to completion and the reaction mixture was concentrated onto silica gel. Flash chromatography afforded the title compound (0.80 g, 64%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 10.23 (s, 1H), 9.40 (bs, 1H), 8.45 (s, 1H), 8.33-8.31 (m, 1H), 8.19 (d, J=5.5 Hz, 1H), 8.07-8.03 (m, 1H), 7.83-7.79 (m, 1H), 7.74-7.70 (m, 1H), 7.60 (at, J=7.9 Hz, 1H), 7.48-7.35 (m, 3H), 7.24-7.16 (m, 2H), 7.00-6.94 (m, 1H), 6.67 (d, J=2.2 Hz, 1H), 6.50-6.44 (m, 2H), 3.79 (s, 3H), 3.75-3.68 (m, 2H), 3.25 (t, J=6.6 Hz, 2H), 3.01 (s, 3H), 2.70-2.60 (m, 5H), 2.45-2.24 (m, 5H), 1.86-1.79 (m, 2H), 1.55-1.44 (m, 2H). MS (ES+, m/z) 822 (M+1).

Provenance & Evidence