Reaction Steps
5-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was prepared from 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (3.00 g, 14.0 mmol) and phenyl boronic acid (1.8 g, 15.0 mmol), in a manner analogous to Step 73c. The product was isolated as a white powder (0.567 g, 19%) after chromatography on an Isco silica gel column (80 g) using methanol in dichloromethane as the eluent. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 7.94 (d, J=6.9 Hz, 2H), 7.52 (m, 4H), 7.37 (m, 1H), 7.02 (d, J=6.5 Hz, 1H), 6.02 (s, 2H). MS=210 (MH)+. 76b) (5-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine was prepared from 5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (100.0 mg, 0.476 mmol) and 1-[2-(4-bromo-phenoxy)-ethyl]-pyrrolidine (119 μl, 0.571 mmol) in a manner analogous to Example 75. The title compound (5-Phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine was isolated as the TFA salt as a off white solid (0.0037 g, 2%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 10.05 (br s, 1H), 9.48 (s, 1H), 8.04 (d, J=8.5 Hz, 2H), 7.61 (m, 7H), 7.18 (d, J=7.5 Hz, 1H), 6.95 (d, J=8.5 Hz, 2H), 4.25 (m, 2H), 3.80-3.40 (m, 4H), 3.12 (m, 2H), 2.03 (m, 2H), 1.89 (m, 2H). MS=400 (MH)+.
