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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1534655Generated: October 26, 2026

1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

https://huagongshe.com/reaction/1534655

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 535414—
Reactant1,2,3,4,5,6-Hexahydropyrrolo[3,4-c]pyrrole dihydrobromideHCID 23282849—
SolventAcetonitrileHCID 6342—
Product1-Cyclopropyl-7-[3,7-diazabicyclo[3.3.0]oct-1(5)-en-3-yl]-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 986430567%

Reaction Steps

The solution of 0.4 g of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 0.8 g of 3,7-diazabicyclo[3.3.0]oct-1(5)-ene dihydrobromide, and 0.8 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in 30 ml of acetonitrile was refluxed in oil bath at the temperature of 100° C. for 8 hours, and this reaction mixture was kept overnight at the room temperature. The product precipitate was filtered off and then the residue was washed with methanol, to obtain 0.35 g of the title compound (yield 67%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05089621
Source datasetuspto-grants-1992_02
ORD IDord-38188f7c14414c6c88eb1ce5604e19bc
Source noteuspto-grants-1992_02