Diisopropylethylamine → tert-Butyl (4-(5-(8-morpholino-2-((quinolin-2-ylthio)methyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)piperazin-1-yl)sulfonylcarbamate

Participants

Reaction Steps

Compound 6 (137 mg, 0.612 mmol) was placed in an 8 mL vial equipped with a stir bar and then DCM (1 mL) and DIEA (68.2 μL, 0.486 mmol) were added. (tert-Butoxycarbonyl)((4-(dimethyliminio)pyridin-1(4H)-yl)sulfonyl)amide (48.8 mg, 0.162 mmol) was added as a solid and the reaction was stirred at rt for 3 h and then the solvent was removed under reduced pressure. The crude product was chromatographed on a 12 g SiO2 pre-packed column eluting with 0-100% EtOAc/heptane. The resulting product was chromatographed on a 12 g SiO2 pre-packed column eluting with 0-80% EtOAc/heptane to afford the title compound 31a. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.55 (d, J=2.2 Hz, 1H), 7.96 (d, J=5.6 Hz, 1H), 7.80-7.92 (m, 3H), 7.71 (d, J=8.1 Hz, 1H), 7.58-7.66 (m, 1H), 7.29-7.48 (m, 2H), 7.24 (d, J=8.8 Hz, 1H), 6.70 (d, J=8.8 Hz, 1H), 6.04 (d, J=5.9 Hz, 1H), 4.85 (s, 2H), 3.89-4.00 (m, 4H), 3.80-3.89 (m, 4H), 3.62-3.73 (m, 4H), 1.47 (s, 9H).

Provenance & Evidence