4-Azidooxane → HCID 117777715, compound

Participants

Reaction Steps

A mixture N-(5-(6-ethynyl-3H-imidazo[4,5-b]pyridin-3-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (250 mg, 0.644 mmol), 4-azidotetrahydro-2H-pyran (90 mg, 0.77 mmol, 1.2 eq.), copper iodide (12 mg, 0.06 mmol, 0.1 eq.) in DMF was stirred at 90° C. for 16 h. The mixture was quenched with water and the precipitate formed was filtered and dried to give the crude product which was purified by preparative HPLC to give the product in 45% yield (150 mg). 1H NMR (300 MHz, DMSO): δ 10.4 (s, 1H), 8.99-8.97 (m, 2H), 8.88 (s, 1H), 8.61-8.60 (m, 1H), 8.32-8.29 (m, 1H), 7.91 (d, 1H), 7.76-7.68 (m, 2H), 7.48-7.41 (m, 1H), 7.3-7.24 (m, 1H), 4.80 (m, 1H), 4.02 (m, 2H), 3.50-3.60 (m, 2H), 2.10 (s, 3H), 2.0-2.12 (m, 4H); LC-MS (ESI): Calculated mass: 515.5; Observed mass: 516.5 [M+H]+ (rt: 1.37 min).

Provenance & Evidence