Ethyl Acetate → HCID 89714577, compound

Participants

Reaction Conditions

Reaction Steps

13 mg of lithium aluminium hydride (0.34 mmol) are placed in 5 ml of anhydrous THF. A solution containing 90 mg (0.17 mmol) of 3-[4-[4-(3-ethylureido)phenyl]-8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-7,8-dihydro-5H-9-oxa-1,3,6-triazabenzocyclohepten-6-yl]propionic acid in 10 ml of THF is added dropwise. The reaction mixture is heated at 66° C. for 18 hours. 72 mg of lithium aluminium hydride (1.89 mmol) are added and the mixture is heated for a further 24 hours at 66° C. The medium is then cooled in an ice-water bath to 4° C. and basified with saturated aqueous Na2SO4 solution. Ethyl acetate is added and the mixture is filtered through Celite, rinsed with ethyl acetate and concentrated. The residue is chromatographed on silica gel with a gradient of MeOH containing 10% aqueous ammonia DCM ranging from 0% to 10%. The solid is rinsed with acetonitrile and then with pentane to give 22 mg of 1-ethyl-3-{4-[6-(3-hydroxypropyl)-8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl]phenyl}urea.

Provenance & Evidence