Reaction Steps
To [8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine (0.256 g, 0.664 mmol) in N,N-dimethylformamide (10 mL) under an atmosphere of nitrogen was added potassium carbonate (0.275 g, 1.99 mmol), 2-chloroethyl methyl sulfide (0.0982 mL, 0.996 mmol), followed by sodium iodide (0.0996 g, 0.664 mmol) was heated at 70° C. overnight and cooled to room temperature. The reaction was diluted with ethyl acetate, washed with water several times, washed with brine, dried over sodium sulfate, and concentrated. The product was purified using Prep TLC plates (5% methanol in dichloromethane) and concentrated to give [8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-[3-(2-methylsulfanyl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-amine (0.173 g, 57%). MS=460 (MH)+. 314b) To [8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-[3-(2-methylsulfanyl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-amine (0.173 g, 0.376 mmol) in methanol (5 mL) was added oxone (0.694 g, 1.13 mmol) in water (2.5 mL) and was stirred at room temperature for 2 hours and concentrated. The reaction was partitioned between dichloromethane/1N sodium carbonate, washed with water/brine, dried over sodium sulfate, and concentrated. The product was purified using Prep TLC plates (5% methanol in dichloromethane) and concentrated to give [3-(2-methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-[8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-amine (0.025 g, 14%). MP=91-94° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.52 (s, 1H), 8.75 (d, 1H), 7.55 (m, 2H), 7.40 (m, 2H), 7.32 (s, 1H), 7.18 (d, 1H), 7.05 (m, 3H), 3.75 (s, 3H), 3.28 (m, 2H), 3.18 (s, 3H), 2.85 (m, 2H), 2.75 (m, 4H), 2.58 (m, 4H): MS=492 (MH)+.
