p-Toluenesulfonic acid → N-(2,6-difluorophenyl)-3-(3-(2-(2-methoxy-4-(4-(4-(methylsulfonyl)piperazin-1-yl)piperidin-1-yl)phenylamino)pyrimidin-4-yl)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) (1.00 g, 2.2 mmol), 2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (0.80 g, 2.2 mmol), p-toluenesulfonic acid (0.99 g, 5.2 mmol) and iPrOH (20 mL) was heated in the microwave at 175° C. for 20 min. LCMS indicated the reaction had proceeded to completion and the reaction mixture was concentrated onto silica gel. Flash chromatography afforded the title compound (1.1 μg, 65%) 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=5.2 Hz, 1H), 8.07-8.03 (m, 1H), 7.83-7.80 (m, 1H), 7.74-7.71 (m, 1H), 7.60 (at, J=7.7 Hz, 1H), 7.48-7.35 (m, 3H), 7.23-7.17 (m, 2H), 7.01-6.95 (m, 1H), 6.67 (d, J=2.5 Hz, 1H), 6.50-6.44 (m, 2H), 3.79 (s, 3H), 3.76-3.70 (m, 2H), 3.11-3.06 (m, 4H), 2.85 (s, 3H), 2.71-2.63 (m, 2H), 2.62-2.57 (m, 4H), 2.46-2.36 (m, 2H), 1.87-1.79 (m, 2H), 1.60-1.47 (m, 2H). MS (ES+, m/z) 794 (M+1).

Provenance & Evidence