Triethylamine → HCID 66744380, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-bromo-pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (153 mg, 0.23 mmol) and 1-(3,7-diazaspiro[4.4]nonan-3-yl)propan-1-one (101 mg, 0.46 mmol) in DMF (2 mL) was added Et3N (70 mg, 97 μL, 0.70 mmol). The reaction vessel was sealed and heated at 90° C. for 40 minutes. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed with brine (2×). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using 0-60% EtOAc in DCM to yield tert-butyl N-[[4-[5-[3[bis(tert-butoxycarbonyl)amino]-6-(3-propanoyl-3,7-diazaspiro[4.4]nonan-7-yl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (133 mg, 75%). LC/MS m/z 763.9 [M+H]+.

Provenance & Evidence