Dimethylformamide → HCID 89714584, compound

Participants

Reaction Conditions

Reaction Steps

50 mg (83.38 μmol) of {4-[8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-6-(tetrahydropyran-4-yl)-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl]phenyl}carbamic acid phenyl ester are placed in a microwave reactor and 25 mg (0.25 mmol) of 5-methylisoxazol-3-ylamine are added. 2 ml of DMF and 1 ml of THF are added. The reaction mixture is heated in a Biotage microwave machine for 30 minutes at 100° C. 100 mg (1.0 mmol) of 5-methylisoxazol-3-ylamine are added and the mixture is heated for 2 hours at 110° C. A further 300 mg (3 mmol) of 5-methylisoxazol-3-ylamine are added and the mixture is heated for 2 hours at 110° C. The solvents are evaporated off. The residue is taken up in water and the insoluble material is filtered off, washed three times with water, taken up in MeOH/DCM and dried. The residue is chromatographed on silica gel, eluting with an MeOH/DCM mixture from (0/100 v/v) up to (5/95 v/v) to give 6 mg of 1-{4-[8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-6-(tetrahydropyran-4-yl)-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl]phenyl}-3-(5-methylisoxazol-3-yl)urea.

Provenance & Evidence