112811-66-2

Usage

Uses

Used in Organic Synthesis:
2,4,5-Trifluoro-3-methoxybenzoyl chloride is utilized as a reagent in organic synthesis for the purpose of introducing the benzoyl group into a variety of organic molecules. Its unique substitution pattern allows for specific chemical reactions that are valuable in the creation of complex organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,4,5-Trifluoro-3-methoxybenzoyl chloride serves as an intermediate. It plays a crucial role in the synthesis of various pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, 2,4,5-Trifluoro-3-methoxybenzoyl chloride is employed as an intermediate. Its involvement in the synthesis process is essential for creating agrochemicals that can be used in agriculture to protect crops and enhance yields.
Given the strong reactivity of 2,4,5-Trifluoro-3-methoxybenzoyl chloride, it is imperative that it is handled with care, typically by trained professionals in controlled laboratory environments to ensure safety and achieve desired outcomes in chemical reactions.

InChI:InChI=1/C8H4ClF3O2/c1-14-7-5(11)3(8(9)13)2-4(10)6(7)12/h2H,1H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 112811-65-1 3-methoxy-2,4,5-trifluorobenzoic acid 
• 652-03-9 3,4,5,6-tetrafluorophthalic acid 
• 136897-64-8 methyl 3-methoxy-2,4,5-trifluorobenzoate 
• 116751-24-7 2,4,5-trifluoro-3-hydroxybenzoic acid 
• 33795-85-6 N-methyl-tetrafluorophthalimide 
• 13332-24-6 1-bromo-3-methoxy-2,4,5-trifluorobenzene 
• 112811-63-9 3-methoxy-2,4,5-trifluorobenzonitrile 
• 112811-64-0 2,4,5-trifluoro-3-methoxy-benzamide 

Downstream Products

• 112811-68-4 ethyl 3-methoxy-2,4,5-trifluorobenzoylacetate 
• 925457-02-9 ethyl α(E)-[(diethylamino)methylene]-2,4,5-trifluoro-3-methoxy-β-oxo-benzenepropanoate 
• 112811-67-3 diethyl 3-methoxy-2,4,5-trifluorobenzoylmalonate 
• 121577-35-3 Ethyl 3-dimethylamino-2-(3-methoxy-2,4,5-trifluorobenzoyl) acrylate 
• 1357168-49-0 N-[3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]-3-methoxy-2,4,5-trifluorobenzamide 
• 112811-64-0 2,4,5-trifluoro-3-methoxy-benzamide 
• 351367-89-0 N-(cyclopropylcarbomoyl)-2,4,5-trifluoro-3-methoxybenzamide 
• 112811-60-6 1-Cyclopropyl-6-fluoro-8-methoxy-7-(3-amino-1-pyrrolidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 160738-57-8 gatifloxacin 
• 112811-72-0 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid 
• 112811-75-3 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylaminomethyl-1-pyrrolidinyl)-4-oxo-3-quinolinecarboxylic acid 
• 112811-71-9 ethyl 8-methoxy-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate 

Relevant academic research and scientific papers

Practical synthesis and molecular structure of a potent broad-spectrum antibacterial isothiazoloquinolone

We report the synthesis of the new 2-sulfonylquinolone ethyl 1-cyclopropyl-6,7-difluoro-2-methanesulfonyl-8-methoxy-4-oxo-1, 4-dihydroquinoline-3-carboxylate (5). Sulfone 5 is a key intermediate used in the optimized synthesis of the isothiazoloquinolone 9-cyclopropyl-6-fluoro-8- methoxy-7-(2-methylpyridin-4-yl)-9H-isothiazolo[5,4-b]quinoline-3,4-dione (1), a potent broad-spectrum antibacterial agent that is effective against clinically important resistant organisms such as methicillin-resistant Staphylococcus aureus (MRSA). Our synthetic method is free of chromatographic purification and amenable to large-scale synthesis. The molecular structures of 1, 9-cyclopropyl-6,7-difluoro-8-methoxy-9H-isothiazolo[5,4-b]quinoline-3,4-dione (4), 5, and ethyl 2-cyclopropylamino-6,7-difluoro-8-methoxy-4-oxo-4H- thiochromene-3-carboxylate (10) were established unambiguously using multinuclear NMR spectroscopy and X-ray crystallography.

Quinolone dimers as potential antibacterial agents

A series of novel 6-fluoro1,4-dihydro-4-oxo-3-quinoline carboxylic acid dimers (34-37), were synthesized as potential antibacterial agents from commercially available fluoro benzoic acids.

COMPOUNDS TARGETING RNA-BINDING PROTEINS OR RNA-MODIFYING PROTEINS

The invention relates to a compound represented by Formula (I): or a pharmaceutically acceptable salt thereof, compositions comprising the same and methods of preparing and using the same. The variables are described herein.

Preparation method of 2,4,5-trifluoro-3-methoxybenzoyl chloride and intermediate thereof

The invention discloses a preparation method of 2,4,5-trifluoro-3-methoxybenzoyl chloride and intermediate thereof. The preparation method of 2,4,5-trifluoro-3-methoxybenzoyl chloride comprises the following steps: by taking tetrafluorophthalic acid as a raw material, carrying out defluorination hydroxylation and acidification decarboxylation to obtain 2,4,5-trifluoro-3-hydroxybenzoic acid, thenreacting with dimethyl carbonate to obtain 2,4,5-trifluoro-3-methoxybenzoic acid, and finally carrying out acylating chlorination to obtain 2,4,5-trifluoro-3-methoxybenzoyl chloride. The preparation process is simple, the total reaction yield is high, the product quality is good, the process route is environment-friendly, and the method has a good industrial application prospect.

Identification of an ethyl 5,6-dihydropyrazolo[1,5-c]quinazoline-1-carboxylate as a catalytic inhibitor of DNA gyrase

Fluoroquinolones are a class of antibacterial agents used clinically to treat a wide array of bacterial infections and target bacterial type-II topoisomerases (DNA gyrase and topoisomerase IV). Fluoroquinolones, however potent, are susceptible to bacterial resistance with prolonged use, which limits their use in the clinic. Quinazoline-2,4-diones also target bacterial type-II topoisomerases and are not susceptible to bacterial resistance similar to fluoroquinolones, however, their potency pales in comparison to fluoroquinolones. To meet the increasing demand for antibacterial development, nine modified quinazoline-2,4-diones were developed to probe quinazoline-2,4-dione structure modification for possible new binding contacts with the bacterial type-II topoisomerase, DNA gyrase. Evaluation of compounds for inhibition of the supercoiling activity of DNA gyrase revealed a novel ethyl 5,6-dihydropyrazolo[1,5-c]quinazoline-1-carboxylate derivative as a modest inhibitor of DNA gyrase, having an IC50 of 3.5 μM. However, this ethyl 5,6-dihydropyrazolo[1,5-c]quinazoline-1-carboxylate does not trap the catalytic intermediate like fluoroquinolones or typical quinazoline-2,4-diones do. Thus, the ethyl 5,6-dihydropyrazolo[1,5-c]quinazoline-1-carboxylate derivative discovered in this work acts as a catalytic inhibitor of DNA gyrase and therefore represents a new structural type of catalytic inhibitor of DNA gyrase.

Synthesis method of gatifloxacin cyclic ester

The invention belongs to a production process of a pharmaceutical intermediate, and particularly discloses a synthesis method of gatifloxacin cyclic ester. The synthesis method comprises the followingsteps: performing hydrolysis, decarboxylation and methylation on 3, 4, 5, 6-tetrafluoro-N-methylphthalimide serving as a starting material to obtain 2,4,5-trifluoro-3-methoxybenzoyl chloride, coupling the 2,4,5-trifluoro-3-methoxybenzoyl chloride with N,N-ethyl dimethylaminoacrylate, then replacing with cyclopropylamine, and finally performing cyclization to produce the gatifloxacin cyclic esterunder the action of DMF and potassium fluoride. The reaction route is short, the raw materials are wide in source; furthermore, the reaction conditions are mild and easy to operate and control, whichreduces the consumption of the raw materials, facilitates the post-treatment and reduces the cost; potassium fluoride used instead of potassium carbonate in the reaction can not only reduce productionof exhaust gas, but also make the used potassium fluoride used continuously through adjustment by potassium hydroxide, and the cost is further reduced.

Novel fluoroquinolones and use thereof to treat bacterial infections

The present invention relates to novel fluoroquinolones possessing a piperazine moiety substituted by a long alkyl chain, pharmaceutical compositions or medicament containing them and use thereof to treat bacterial infection.

Synthesis, antimycobacterial and antibacterial evaluation of l-[(1R, 2S)-2-fluorocyclopropyl]fluoroquinolone derivatives containing an oxime functional moiety

A series of novel 1-[(1R, 2S)-2-fluorocyclopropyl]fluoroquinolone derivatives 9aed containing an oxime functional moiety were synthesized and evaluated for their biological activity. Our results reveal that 9a1 and 9b3 have good in vitro activity against MTB H37Rv ATCC 27294 (MIC: 0.25 mg/mL) and two MDR-MTB clinical isolates (MICs: 0.065-0.125 mg/mL). Most of 9aed show potent activity against Escherichia coli and Klebsiella pneumoniae (MICs: 50s: 11.43-26.04 mg/kg).

Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold

A series of novel anthranilic diamides with benzyl sulfide scaffold were synthesized, in which N-pyridylpyrazole moiety generally regarded as key pharmacophore was abandoned. The target compounds were characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The preliminary bioassays indicated that half of the title compounds were endowed with good insecticidal activities against armyworm (Mythimna sepatara) at the concentration of 500 mg/L. Exhilaratingly, the synthesized compound 3a was also active against Tetranychus cinnabarinus at 100 mg/L. The difference in activities between the target compounds was influenced by the substituents, which provided some hints for further investigation on structure modifications.

Synthesis of gatifloxacin derivatives and their biological activities against Mycobacterium leprae and Mycobacterium tuberculosis

Novel 3′-piperazinyl derivatives of the 8-hydrogeno and 8-methoxy-6-fluoro-1-cyclopropyl-4-quinolone-3-carboxylic acid scaffolds were designed, synthesized and characterized by 1H, 13C and 19F NMR, and HRMS. The activity of these derivatives against pathogenic mycobacteria (M. leprae and M. tuberculosis), wild-type (WT) strains or strains harboring mutations implicated in quinolone resistance, were determined by measuring drug concentrations inhibiting cell growth (MIC) and/or DNA supercoiling by DNA gyrase (IC50), or inducing 25% DNA cleavage by DNA gyrase (CC25). Compound 4 (with a methoxy in R8 and a secondary carbamate in R3′) and compound 5 (with a hydrogen in R8 and an ethyl ester in R3′) displayed biological activities close to those of ofloxacin but inferior to those of gatifloxacin and moxifloxacin against M. tuberculosis and M. leprae WT DNA gyrases, whereas all of the compounds were less active in inhibiting M. tuberculosis growth and M. leprae mutant DNA gyrases. Since R3′ substitutions have been poorly investigated previously, our results may help to design new quinolone derivatives in the future.