Ammonia → N-(2,6-difluorophenyl)-2-(methyloxy)-5-{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

5-[3-(2-Chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-(methyloxy)benzamide (Intermediate Example 2) (100 mg, 0.2 mmol), 2-(methyloxy)-4-[4-(methylsulfonyl)-1-piperazinyl]aniline (Example 232, step B) (51 mg, 0.18 mmol), and p-toluenesulfonicacid (93 mg, 0.49 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 (96 mg, 0.12 mmol, 69%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.78 (s, 1H), 9.37 (s, 1H), 8.48 (s, 1H), 8.21 (d, J=5.13 Hz, 1H), 8.10 (d, J=1.83 Hz, 1H), 7.77 (dd, J=8.61, 2.02 Hz, 1H), 7.69 (d, J=8.80 Hz, 1H), 7.36-7.48 (m, 3H), 7.28 (d, J=8.43 Hz, 1H), 7.18 (t, J=8.07 Hz, 2H), 6.96 (t, J=6.78 Hz, 1H), 6.73 (d, J=2.20 Hz, 1H), 6.49-6.57 (m, 2H), 3.98 (s, 3H), 3.81 (s, 3H), 3.25 (br. s., 8H), 2.92 (s, 3H); MS (ESI): 741 [M+H]+.

Provenance & Evidence