Ammonia → N-(2,6-difluorophenyl)-5-(3-{2-[(5-methyl-2-(methyloxy)-4-{4-[2-(methyloxy)ethyl]-1-piperazinyl}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)-2-(methyloxy)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) (200 mg, 0.4 mmol), 5-methyl-2-(methyloxy)-4-{4-[2-(methyloxy)ethyl]-1-piperazinyl}aniline (Example 241, step B) (102 mg, 0.37 mmol) and p-toluenesulfonicacid (185 mg, 0.98 mmol) were weighed into a 20 mL vial. 2 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 (125 mg, 0.17 mmol, 47%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.75 (s, 1H), 9.33 (s, 1H), 8.43 (s, 1H), 8.20 (d, J=5.31 Hz, 1H), 8.07 (d, J=1.83 Hz, 1H), 7.74 (dd, J=8.70, 1.74 Hz, 1H), 7.66 (d, J=8.97 Hz, 1H), 7.45 (s, 1H), 7.33-7.45 (m, 2H), 7.25 (d, J=8.79 Hz, 1H), 7.15 (t, J=8.06 Hz, 2H), 6.89-6.95 (m, 1H), 6.74 (s, 1H), 6.53 (d, J=5.13 Hz, 1H), 3.95 (s, 3H), 3.76 (s, 3H), 3.43 (t, J=5.77 Hz, 2H), 3.21 (s, 3H), 2.83 (t, J=4.40 Hz, 4H), 2.47-2.58 (m, 6H), 2.11 (s, 3H); MS (ESI): 735 [M+H]+.

Provenance & Evidence