Ammonia → N-(2,6-difluorophenyl)-3-{3-[2-({5-methyl-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), 5-methyl-2-(methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline (Example 225, step B) (53 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 (67 mg, 0.092 mmol, 52%). 1H NMR (400 MHz, DMSO-d6) d ppm 10.23 (s, 1H), 9.40 (s, 1H), 8.50 (s, 1H), 8.33 (s, 1H), 8.24 (d, J=5.50 Hz, 1H), 8.05 (d, J=7.70 Hz, 1H), 7.82 (d, J=8.07 Hz, 1H), 7.73 (d, J=9.17 Hz, 1H), 7.61 (t, J=7.70 Hz, 1H), 7.53 (s, 1H), 7.45-7.51 (m, 1H), 7.36-7.44 (m, 1H), 7.20 (t, J=8.07 Hz, 2H), 7.00 (t, J=6.97 Hz, 1H), 6.83 (s, 1H), 6.51 (d, J=5.13 Hz, 1H), 3.81 (s, 3H), 3.23-3.30 (m, 4H), 2.95-2.99 (m, 4H), 2.94 (s, 3H), 2.17 (s, 3H); MS (ESI): 725 [M+H]+.

Provenance & Evidence