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4-bromo-N-(6-chloroimidazo[1,2-b]pyridazin-3-yl)butanamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
74%
With pyridine; In tetrahydrofuran; at 20℃; for 1.0h;
To 1.0 g (5.930 mmol) of <strong>[166176-45-0]6-chloroimidazo[1,2-b]pyridazin-3-amine</strong> dissolved in 15 ml of THFwas added 4-bromobutanoyl chloride (1.21 g, 6.52 mmol) and pyridine (0.96 ml, 11.86 mmol). Thismixture was stirred for 1 hr at rt, and then diluted with 30 ml EtOAc and quenched with aq. NaHC03.The organic layer was separated and washed with brine, dried over MgS04, and concentrated. The10 solid obtained (1.39 g, 7 4% yield) was pure enough to be used for the next step without furtherpurification.
To a solution <strong>[166176-45-0]6-chloroimidazo[1,2-b]pyridazin-3-amine</strong> and triethylamine (0.8 ml, 6.0 mmol)in DCM (25 ml) was added acetyl chloride dropwise and stirred at rt for overnight. The mixture was30 concentrated and purified by ISCO column chromatography (10% MeOH/DCM) to give not very pure N-(6-chloroimidazo[1,2-b]pyridazin-3-yl)acetamide (500 mg, 95% yield). 60 mg of non-pure materialwas further purified by Prep HPLC (neutral) to give pure N-(6-chloroimidazo[1,2-b]pyridazin-3-yl)acetamide. 1H NMR (400 MHz, METHANOL-d4) 8 ppm 8.01 (d, J=9.35 Hz, 1 H), 7.94 (s, 1 H), 7.26(d, J=9.35 Hz, 1 H), 2.29 (s, 3 H); LRMS (ESI) mje 210.9 [(M +H)+, calcd for CsHsCIN40 211.6].
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