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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1534823Generated: November 2, 2026

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

https://huagongshe.com/reaction/1534823

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—
ReactantN-ethyl-3,7-diazabicyclo [3.3.0] oct-1(5)-ene dihydrobromideHCID 19908239—
SolventAcetonitrileHCID 6342—
Product1-Cyclopropyl-6,8-difluoro-7-[7-ethyl-3,7-diazabicyclo [3.3.0] oct-1(5)-en-3-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 1990824173.5%

Reaction Steps

1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.48 g), N-ethyl-3,7-diazabicyclo [3.3.0] oct-1(5)-ene dihydrobromide (0.57 g) and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU, 0.87 ml) were dissolved in acetonitrile (20 ml) and refluxed for 3 hours. After cooling the reaction mixture, the produced precipitate was collected by filteration and washed with acetonitrile (10 ml) and methanol (10 ml) to give the title compound (0.5 g, yield 73%)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05091384
Source datasetuspto-grants-1992_02
ORD IDord-59be8c569d694dd39628bbb6f1c90981
Source noteuspto-grants-1992_02