Dimethyl Sulfoxide → HCID 68827797, compound

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Reaction Steps

A mixture of 6-chloropyridazine-3-carbonitrile (291 mg, 2.12 mmol) (Szilagyi, G., et al; European J. Med. Chem. 19:111-117, 1984), sodium azide (149 mg, 2.29 mmol), and DMSO (0.9 mL) was stirred at rt for 20 min, then diluted with water (10 mL), and extracted with EtOAc (3×10 mL). The organic layers were combined, washed with brine (1×10 mL), dried (Na2SO4), and the clear pink solution was passed through a silica plug (EtOAc eluent). Treatment with decolorizing charcoal, filtration, and concentration with rotary evaporation afforded the title compound as an off-white solid (243 mg, 1.69 mmol, 80% yield). 1H-NMR (300 MHz, CDCl3) δ 8.66 (d, J=9.3 Hz, 1H), 7.81 (d, J=9.3 Hz, 1H).

Provenance & Evidence