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

Participants

Reaction Conditions

Reaction Steps

3-[3-(2-Chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)benzamide (Intermediate Example 1) (100 mg, 0.22 mmol), 2-(methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline (Example 232, step B) (51 mg, 0.18 mmol), and p-toluenesulfonicacid (99 mg, 0.52 mmol) were weighed into a 20 mL vial. 1 mL of trifluoroethanol was added and the mixture was heated to 100° C. for 72 h. 2 mL of 2 N ammonia in MeOH was added. The solvent was rotovaped down. The residue was taken up in 3 mL of DCM. 1 g of silica gel was added. The solvent was rotovaped down and the pre-absorbed solids were purified by flash chromatography to give the title compound (92 mg, 0.13 mmol, 73%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.24 (s, 1H), 9.40 (s, 1H), 8.49 (s, 1H), 8.33 (s, 1H), 8.21 (d, J=5.13 Hz, 1H), 8.05 (d, J=7.70 Hz, 1H), 7.82 (d, J=7.70 Hz, 1H), 7.73 (d, J=8.80 Hz, 1H), 7.61 (t, J=7.70 Hz, 1H), 7.43-7.49 (m, 2H), 7.35-7.43 (m, 1H), 7.16-7.24 (m, 2H), 6.99 (t, J=6.78 Hz, 1H), 6.73 (d, J=2.20 Hz, 1H), 6.52 (dd, J=8.62, 2.38 Hz, 1H), 6.48 (d, J=5.13 Hz, 1H), 3.81 (s, 3H), 3.25 (br. s., 8H), 2.92 (s, 3H); MS (ESI): 711 [M+H]+.

Provenance & Evidence