1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Ethyl-6-fluoro-1,4-dihydro-7-(3-methyl-3,8-diazabicyclo[3.2.1]oct-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid, hydrochloride

Participants

Reaction Steps

A mixture of 0.54 g (2.0 mmol) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 0.50 g (2.5 mmol) of 3-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride [P. A. Sturm, et al, J. Med. Chem., 17, 481 (1974)], 0.75 ml (5.0 ml) 1,8-diazabicyclo[5.4.0]undec-7-ene and 20 ml of acetonitrile was heated under reflux for 1.5 hours and stirred overnight at room temperature. The reaction mixture was filtered and the solid washed with ethanol to give 0.46 g of the title compound, mp>310°.

Provenance & Evidence