Reaction Steps
According to General Protocol III, 4,5-difluoro-2-[4(2-{[2-(methyloxy)-4-(1-propyl-1,2,5,6-tetrahydro-3-pyridinyl)phenyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide was prepared from 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-4,5-difluorobenzamide (0.300 g, 0.630 mmol), 27% aqueous ammonium hydroxide, and 2-(methyloxy)-4-(1-propyl-1,2,5,6-tetrahydro-3-pyridinyl)aniline (0.250 g, 0.950 mmol) and isolated as a yellow solid (0.040 g, 12% Yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.89 (t, J=7.14 Hz, 3H), 1.54 (s, 2H), 1.74 (s, 2H), 2.25 (s, 2H), 2.42 (s, 2H), 3.26 (s, 2H), 3.88 (s, 3H), 6.14 (s, 1H), 6.23-6.32 (m, 1H), 6.93 (d, J=7.69 Hz, 1H), 7.02 (s, 2H), 7.76 (s, 1H), 7.91 (dd, J=1.65, 0.92 Hz, 1H), 7.97 (dd, J=11.72, 8.79 Hz, 1H), 8.12 (d, J=8.42 Hz, 1H), 8.33 (s, 1H), 9.08 (dd, J=14.65, 7.69 Hz, 1H), 11.43 (s, 1H), 12.25 (s, 1H). ESI-MS (M+H) 533. Retention time 1.75 minutes.
