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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 743638Generated: October 30, 2026

Water → 8-(3-Dimethylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo1,4-dihydrobenzo[b][1,8]naphthyridine

https://huagongshe.com/reaction/743638

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium CarbonateHCID 10340—
Reactant3-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 9839987—
ReactantN,N-dimethylazetidin-3-amine dihydrochlorideHCID 22121220—
SolventDimethyl SulfoxideHCID 679—
Product8-(3-Dimethylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo1,4-dihydrobenzo[b][1,8]naphthyridineHCID 1942373879.9%

Reaction Conditions

Temperature95 °C

Reaction Steps

A suspension of 2 g of 3-ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine, 1.2 g of 3-(dimethylamino)azetidine dihydrochloride and 1.5 g of sodium carbonate in 30 cm3 of dimethyl sulphoxide is heated with stirring to a temperature in the region of 95° C. for 5 hours. After cooling to approximately 20° C., the reaction mixture is treated with 60 cm3 of water. The insoluble matter is drained and washed with 3 times 20 cm3 of water. 2 g of 8-(3-dimethylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine are obtained in the form of a yellow solid, melting point 224° C., which is used without further purification for the subsequent steps.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05556861
Source datasetuspto-grants-1996_09
ORD IDord-36de64b5b2d542e599da2546da480dd1
Source noteuspto-grants-1996_09