Reaction Steps
8-Pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from 8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1.0 g, 4.7 mmol) and 3-pyridylboronic acid (0.81 g, 6.6 mmol) in a manner analogous to Step 2c. The product of the reaction was isolated as a white solid (0.92 g, 93%). MP=185-187° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.28 (d, J=2.1 Hz, 1H), 8.62-8.58 (m, 2H), 8.49 (ddd, J=8.1, 1.8, 1.8 Hz, 1H), 7.82 (dd, J=7.4, 0.7 Hz, 1H), 7.53 (dd, J=8.0, 4.7 Hz, 1H), 7.01 (t, J=7.0 Hz, 1H), 6.18 (br s, 2H). MS=212 (MH)+. 6b) (4-Morpholin-4-yl-phenyl)-(8-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amine and phenyl-(8-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amine were prepared from 8-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (70.0 mg, 0.331 mmol) and 4-(4-bromo-phenyl)-morpholine (100.0 mg, 0.4130 mmol) in a manner analogous to Example 2d. (4-Morpholin-4-yl-phenyl)-(8-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amine was isolated as a yellow solid (0.025 g, 20%). MP=226-228° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 9.16 (d, J=1.9 Hz, 1H), 8.66 (dd, J=4.8, 1.4 Hz, 1H), 8.46-8.41 (m, 2H), 7.61 (dd, J=7.4, 1.1 Hz, 1H), 7.54-7.49 (m, 2H), 7.45 (dd, J=7.9, 4.8 Hz, 1H), 7.00-6.93 (m, 3H), 6.69 (s, 1H), 3.90-3.86 (m, 4H), 3.14-3.09 (m, 4H). MS=373 (MH)+.
