Water → HCID 9949920, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1.16 g of 7,8-difluoro-1-methyl-4-oxo-l,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 1.38 g of 3-aminoazetidine in 15 cm3 of dimethyl sulphoxide is heated with stirring to a temperature in the region of 95° C. for 6 hours. After cooling to approximately 20° C., 100 cm3 of water are added to the reaction mixture. The insoluble matter is drained, washed with 3 times 20 cm3 of water, taken up with 100 cm3 of water and treated with 4 cm3 of N methanesulphonic acid. After removal of some slight insoluble matter by filtration through diatomaceous silica and addition of 4 cm3 of N aqueous sodium hydroxide, the suspension obtained is concentrated under reduced pressure (20 kPa) at a temperature in the region of 60°C. to a volume of approximately 80 cm3. The insoluble matter is drained, washed with 100 cm3 of water and 100 cm3 of ethanol and recrystallized in 150 cm3 of dimethylformamide. 0.7 g of 8-(3-amino-1-azetidinyl)-7-fluoro-1-methyl-4-oxo1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a yellow solid, which decomposes at 358° C.

Provenance & Evidence