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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1589568Generated: October 25, 2026

1,8-Diazabicyclo(5.4.0)undec-7-ene → 10-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid

https://huagongshe.com/reaction/1589568

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant8,9-Difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acidHCID 534278—
Reactant2,5-Diazabicyclo(2.2.2)octane dihydrochlorideHCID 22924390—
SolventAcetonitrileHCID 6342—
Product10-(2,5-Diazabicyclo[2.2.2]oct-2-yl)-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acidHCID 1356584026.8%

Reaction Steps

A solution of 0.56 g (2.0 mmol) of 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 0.41 g (2.2 mmol) of 2,5-diazabicyclo[2.2.2]octane dihydrochloride, 0.90 ml (6.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 25 ml of acetonitrile was heated under reflux for 18 hours. The solution was evaporated to dryness and the residue was triturated with methanol and filtered to give 0.20 g of the title compound, 260°-265° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04571396
Source datasetuspto-grants-1986_02
ORD IDord-004445253279438d81facaf8f68fee8b
Source noteuspto-grants-1986_02