Sodium Iodide → [8-(2-ethoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(2-methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine

Participants

Reaction Conditions

Reaction Steps

To [8-(2-ethoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine (0.200 g, 0.428 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (0.177 g, 1.28 mmol), 1-chloro-2-methanesulfonyl-ethane (0.122 g, 0.856 mmol), followed by sodium iodide (0.0641 g, 0.428 mmol) and was heated at 80° C. overnight and cooled at r.t. The reaction was diluted with ethyl acetate, washed with water several times, dried over sodium sulfate, and concentrated. The product was purified using Prep TLC plates (5% methanol in dichloromethane) and concentrated to give [8-(2-ethoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(2-methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7yl)-amine (0.140 g, 57%). MP=105-109° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.51 (s, 1H), 8.78 (d, 1H), 7.98 (s, 1H), 7.78 (d, 1H), 7.68 (d, 1H), 7.40 (m, 3H), 7.08 (t, 1H), 6.95 (d, 1H), 4.15 (q, 2H), 3.28 (m, 2H), 3.05 (s, 3H), 2.85 (m, 2H), 2.75 (m, 4H), 2.55 (m, 4H), 1.22 (t, 3H): MS=574 (MH)+.

Provenance & Evidence