Methyl iodide → tert-butyl ((1S,3R)-3-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-1,2,2-trimethylcyclopentyl)carbamate

Participants

Reaction Steps

A solution of tert-butyl ((1S,3R)-3-((3-carbamoyl-6-(hydrazinecarbonyl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-1,2,2-trimethylcyclopentyl)carbamate (3.29 g, 7.16 mmol) and 1,1′-thiocarbonyldiimidazole (1.659 g, 9.31 mmol) in THF (25 mL) was heated to 70° C. for 2 hrs. The reaction mixture was added Et3N (2.59 mL, 18.61 mmol) and MeI (0.582 mL, 9.31 mmol) and stirred at RT for 16 hrs which was concentrated and added 150 mL of water which was stirred for 30 minutes. The solid was collected to give the desired tert-butyl ((1S,3R)-3-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-1,2,2-trimethylcyclopentyl)carbamate (2.35 g, 64% yield). LC/MS (M+H)+=516.3.

Provenance & Evidence