7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid synthesis
- Product Name:7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
- CAS Number:100361-18-0
- Molecular formula:C12H8ClFN2O3
- Molecular Weight:282.65
96568-07-9
100361-18-0
Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (0.1 g, 0.32 mmol) was used as a raw material and dissolved in THF (5 ml). Concentrated HCl (45 μL, 0.7 mmol) was added to this solution. The reaction mixture was heated to reflux and the reaction was continued for 2 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the reaction mixture was cooled to room temperature. The precipitated solid was collected by filtration to afford the target product 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid in a yield of 70 mg with 78% yield.
96568-07-9
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100361-18-0
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Yield:100361-18-0 78%
Reaction Conditions:
with hydrogenchloride;water in tetrahydrofuran; for 2 h;Reflux;Inert atmosphere;
Steps:
Compound 2: 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphtyridine-3-carboxylic acid
To a solution of ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphtyridine-3-carboxylate (0.1g, 0.32 mmol) in THF (5 ml) was added conc.HCl (45 μL, 0.7 mmol). The reaction mixture was heated to reflux for 2 h. After completion of the reaction by TLC, reaction mixture was cooled to room temperature. The solid precipitated was filtered to give the title compound as a solid (70 mg, 78%).
References:
Karoli, Tomislav;Mamidyala, Sreeman K.;Zuegg, Johannes;Fry, Scott R.;Tee, Ernest H.L.;Bradford, Tanya A.;Madala, Praveen K.;Huang, Johnny X.;Ramu, Soumya;Butler, Mark S.;Cooper, Matthew A. [Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,# 7,p. 2428 - 2433] Location in patent:supporting information; experimental part
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100361-18-0
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100361-18-0
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100361-18-0
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100361-18-0
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