Sodium Iodide → 2-{7-[5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-N,N-dimethyl-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of [5-(2-Methoxymethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-amine (70.0 mg, 0.18 mmol) in acetonitrile (5 mL) was added potassium carbonate (0.0484 g, 0.350 mmol), 2-chloro-N,N-dimethyl-acetamide (0.0270 mL, 0.263 mmol), followed by sodium iodide (0.0263 g, 0.175 mmol) and the reaction was heated at 70° C. for 2.5 hours and cooled to room temperature. The reaction was diluted with chloroform, washed with water then brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified via flash chromatography utilizing an ISCO automated purification apparatus (basic alumina column and 0%→10% methanol in dichloromethane). Product was isolated as a yellow foam (0.028 g, 32%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.64 (d, J=7.7 Hz, 1H), 7.59-7.42 (m, 5H), 7.27 (m, 1H), 7.23-7.19 (m, 1H), 6.98 (d, J=7.9 Hz, 1H), 6.93 (s, 1H), 6.91-6.87 (m, 1H), 4.35 (br s, 2H), 3.26 (s, 2H), 3.20 (s, 3H), 3.14 (s, 3H), 2.97 (s, 3H), 2.88-2.83 (m, 4H), 2.69-2.63 (m, 4H). MS=485 (MH)+.

Provenance & Evidence