Dimethylformamide dimethyl acetal → N-(2-{[5-(2,6-Dichlorophenyl)-6-oxo-6H-pyrimido[1,6-b]pyridazin-2-yl]sulfanyl}benzyl)-3-fluoro-5-(morpholin-4-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-[2-({6-[2-amino-1-(2,6-dichlorophenyl)-2-oxoethyl]pyridazin-3-yl}sulfanyl)benzyl]-3-fluoro-5-(morpholin-4-yl)benzamide (91 mg, 0.145 mmol) in toluene (4 mL) under an argon atmosphere was treated with DMF-DMA (0.042 mL, 0.315 mmol). The mixture was heated at 100° C. for 1.75 h, then cooled to RT and the precipitate separated by filtration to afford the title compound (77 mg, 84%) as a yellow powder. LCMS (Method 3): Rt 9.8 min, m/z 636 [MH+]. 1H NMR (400 MHz, DMSO-d6): 9.01 (1H, t, J 5.7), 8.82 (1H, d, J 0.7), 7.70 (1H, dd, J 7.7, 1.2), 7.60 (2H, m), 7.58-7.52 (2H, m), 7.49 (1H, dd, J 8.9, 7.3), 7.42 (1H, td, J 7.3, 2), 7.23 (1H, br t, J 1.6), 7.04-6.98 (2H, m), 6.93-6.86 (2H, m), 4.66 (2H, d, J 5.6), 3.73 (4H, t, J 4.7), 3.17 (4H, t, J 4.7).

Provenance & Evidence