Cyanamide → HCID 86729543, compound

Participants

Reaction Steps

17.1 g (50.4 mmol) 3-(1-benzofuran-2-yl)-6-[3-(methylsulfanyl)propoxy]imidazo-[1,2-b]pyridazine and 2.65 g (63.0 mmol) cyanamide were dissolved in 86 mL methanol. At 20-25° C. 7.35 g (65.5 mmol) potassium-tert.-butanolate were added in portions. 11.7 g (65.5 mmol) N-bromosuccinimide were added in portions and it was stirred one hour at room temperature. 250 mL dichloromethane were added and stirred a couple of minutes. 64 mL 10% sodium thiosulfate solution and 22 mL water were added. The layers were separated and the aqueous phase was extracted twice with 30 mL of dichloromethane. The combined organic phases were washed twice with 20 mL water, dried over magnesium sulfate, and concentrated. The residue was crystallized from dichloromethane and tert-butyl methyl ether to yield 12.08 g (63%) of a yellow powder.

Provenance & Evidence