82419-34-9

Basic information

• Product Name: Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate
• Synonyms: Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate;9, 10-Difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid ethyl ester
• CAS NO: 82419-34-9
• Molecular Formula: C₁₅H₁₃F₂NO₄
• Molecular Weight: 309.2648264
• Mol File: 82419-34-9.mol

Chemical Properties

• Melting Point: 261 °C(Solv: ethanol (64-17-5))
• Boiling Point: 442.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.43±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -3.62±0.60(Predicted)
• CAS DataBase Reference: Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate(82419-34-9)
• EPA Substance Registry System: Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate(82419-34-9)

Safety Data

• Hazardous Substances Data: 82419-34-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate is used as a key intermediate in the development of new pharmaceutical compounds. Its structural features make it a valuable building block for the synthesis of various drugs, particularly those targeting specific biological pathways or receptors.
Used in Drug Synthesis:
In the pharmaceutical industry, Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate is employed as a starting material for the synthesis of a wide range of drugs. Its unique structure allows for the creation of diverse drug candidates with potential therapeutic applications.
Used in Medicinal Chemistry:
Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate is utilized in medicinal chemistry for the design and optimization of drug candidates. Its structural properties enable chemists to modify and fine-tune the compound's pharmacological properties, leading to the development of more effective and targeted therapeutic agents.
Used in Drug Discovery:
In the field of drug discovery, Ethyl 9,10-difluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate serves as a valuable tool for identifying potential drug candidates. Its unique structure allows researchers to screen and evaluate its interactions with various biological targets, facilitating the discovery of new therapeutic agents with improved efficacy and safety profiles.

Upstream product

• 118472-61-0 (Z)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethylamino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester 
• 94695-50-8 ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate 
• 924-99-2 ethyl 3-(dimethylamino)acrylate 
• 94695-48-4 2,3,4,5-tetrafluorobenzoyl chloride 
• 74-96-4 ethyl bromide 
• 82419-35-0 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 121996-72-3 6,7-difluoro-8-hydroxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester 
• 82419-33-8 (-)-7,8-difluoro-2,3-dihydro-3-methyl-4H-1,4-benzoxazine 
• 82419-26-9 2,3-difluoro-6-nitrophenol 
• 82419-32-7 3,4-difluoro-2-(2-oxopropyloxy)nitrobenzene 
• 771-69-7 2,3,4-trifluoronitrobenzene 
• 86760-99-8 diethyl [(-)-7,8-difluoro-3-methyl-2,3-dihydro-4H-[1,4]benzoxazin-4-yl]methylenemalonate 
• 107359-16-0 ethyl 6,7,8-trifluoro-1,4-dihydro-1-(1-hydroxyprop-2-yl)-4-oxoquinoline-3-carboxylate 

Downstream Products

• 82419-36-1 ofloxacin 
• 131683-67-5 9-(3-Amino-pyrrolidin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid 
• 82419-52-1 N-Demethylofloxacin 
• 124338-73-4 9-(4-Ethyl-piperazin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid 
• 124255-93-2 8-Fluoro-3-methyl-6-oxo-9-(4-propyl-piperazin-1-yl)-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid 
• 86794-24-3 8-Fluoro-3-methyl-6-oxo-9-(4-phenyl-piperazin-1-yl)-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid 
• 86794-25-4 9-(4-Benzyl-piperazin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid 
• 178912-62-4 (3RS)-10-fluoro-3-methyl-9-(4- methylpiperazin-1-yl)-7-oxo-2,3-dihydro- 7Hpyrido[1,2,3-de]-1,4-benzoxazine-6- carboxylic acid 
• 82419-35-0 9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylic acid 

Relevant articles and documents

UTILISATION DU FLUORURE DE TETRABUTYLAMMONIUM COMME AGENT DE CYCLISATION DANS LA SYNTHESE D'ANTIBACTERIENS DERIVES D'ACIDE PYRIDONE-4-CARBOXYLIQUE-3

It has been found that the Bu4NF/THF base/solvent couple is very efficient in the key cyclization step of (2) to (5) in the synthesis of antibacterial pyridonecarboxylic acid derivatives.In particular chiral intermediate (2d) is directly converted in one

Improved method of preparation process of oxo-fluoro cyclization ester or levo-oxo-fluoro cyclization ester

The invention discloses an improved method of a preparation process of oxo-fluoro cyclization ester or levooxo-fluoro cyclization ester. Existing preparation methods of some levofloxacin intermediateshave many side reactions and are low in yield. According to the technical scheme in the invention, by means of 2,3,4,5-tetrafluorobenzoyl chloride, N,N-dimethylaminoethyl acrylate and (L-)aminopropanol as starting raw materials and toluene and N, N-dimethylformamide added with a water removal agent organic ester or anhydride as solvents, the oxygen-fluorine cyclization ester is prepared through aone-pot reaction. According to the method, organic ester or anhydride is added, so that the loss of raw materials and the generation of by-products are reduced, the reaction yield is increased, the product quality is ensured, and the yield of the (L-)oxo-fluoro cyclization ester can be increased from 75-80% to about 90%.

Preparation method of ofloxacin impurity D

The invention discloses a preparation method of ofloxacin impurity D, and belongs to the field of medicine synthesis. The preparation method has the advantages that the whole technology design is reasonable, the operability is strong, and the purifying is convenient. The preparation method is characterized in that oxygen-fluorine acid is used as an initiating raw material, and is performed with six-step reaction, so as to synthesize the ofloxacin impurity D. The ofloxacin impurity D prepared by the preparation method has the advantages that by screening the optimum preparation steps and reaction conditions through experiment, the purity can reach 99.5% or above; a testing sample is provided for the study of ofloxacin, and the important study value is realized in the clinical pharmacokinetic study.

Ofloxacin preparation method (by machine translation)

The invention provides a preparation method of ofloxacin. The preparation method comprises the following steps of: reacting (N,N)-dimethylamino ethyl acrylate with aminopropanols in methylbenzene; directly adding lewis base serving as a catalyst and trimethylchlorosilane to protect hydroxyl and amido; after reaction is completely finished, dropwise adding (2,3,4,5)-tetrafluorobenzoyl chloride; preserving heat; performing acid washing; removing protecting groups; concentrating an organic layer to obtain an oil layer; adding a proper amount of dimethyl formamide (DMF); diluting and dropwise adding backflow DMF having anhydrous potassium fluoride; recovering DMF and adding water to centrifuge; adding acid water into a solid to hydrolyze to obtain difluorocarboxylic acid; and completely reacting difluorocarboxylic acid and N-methyl piperazine in dimethylsulfoxide (DMSO) by using triethylamine as an acid-binding agent at 90-100 DEG C to obtain ofloxacin. According to the process, hydroxyl and amido are protected by using trimethylchlorosilane, so that the utilization degree of (2,3,4,5)-tetrafluorobenzoyl chloride is effectively increased, and the generation of impurities is reduced to ensure that the reaction yield of intermediate difluorocarboxylic acid is increased by 10 percent.

STRUCTURAL MODIFICATION AND NEW METHODS FOR PREPARATION OF OFLOXACIN ANALOGS

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Trifluorohydroxyaromatic acid and preparation thereof

There are disclosed 2,4,5-Trifluoro-3-hydroxybenzoic acid represented by the following formula (I): STR1 and a salt thereof and a process for preparing the same. Further, there is disclosed a process for preparing 3,5,6-trifluoro-4-hydroxyphthalic acid, which is employed for preparing the above compound.

Antibacterial 1,8-bridged 4-quinolone-3-carboxylic acids

A process for the preparation of a 1,8-bridged 4-quinolone-3-carboxylic acid of the formula STR1 wherein the substituents are defined hereinbelow. Some of the compound are new. The old and new compounds are antibacterials and promote animal growth.

Synthesis and antibacterial activities of substituted 7-oxo-2,3-dihydro-7h-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acids

As part of a search for new synthetic antibacterial agents to combat systemic infection, various analogues of 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acids were synthesized. Among the compounds newly synthesized, 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[ 1,2,3-de][1,4]benzoxazine-6-carboxylic acid (DL-8280) showed potent antibacterial activity against Gram-positive and -negative pathogens, including Psedomonas aeruginosa, and its metabolic disposition was shown in separate experimentals to be favorable.

Benzoxazine derivatives

Pyrido[1,2,3-de][1,4]benzoxazine derivatives are described having the formula (I) STR1 wherein X is a halogen atom, R is a hydrogen atom or an alkyl group of 1 to 6 carbon atoms and Z represents mono-substituted, di-substituted or cyclic-substituted amino group which may contain a hetero atom and may have a substituent such as hydroxyl, alkyl having 1 to 6 carbon atoms, amino, hydroxyalkyl having 1 to 6 carbon atoms or mono- or di-alkylamino having 1 to 6 carbon atoms in each alkyl moiety and the pharmaceutically acceptable salt thereof, having antibacterial activity.