1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 89923259, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-((2-chloro-5-cyano-3-(hydroxymethyl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 402)(120 mg, 0.315 mmol), diphenylphosphoryl azide (0.102 mL, 0.473 mmol) and DBU (0.071 mL, 0.473 mmol) in dry dioxane (3 mL) was heated at 70° C. for 20 hr. It was diluted with EtOAc and washed with water. The aqueous phase was washed with EtOAc and the combined organic phases were washed with brine and dried with sodium sulfate. Removal of the solvents followed by radial silica gel chromatography eluting with DCM containing 0 to 3% MeOH afforded 2-((3-(azidomethyl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (80 mg) as a white solid.

Provenance & Evidence