231285-86-2

Usage

Chemical Properties

White solid

Upstream product

• 571-55-1 ethyl 2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate 
• 60-34-4 methylhydrazine 
• 105486-72-4 5-bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 50-00-0 formaldehyd 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 1067233-79-7 4-trifluoromethyl-N-methylsydnone 
• 623-47-2 propynoic acid ethyl ester 

Downstream Products

• 111493-74-4 ethyl 3-(trifluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate 
• 119083-00-0 1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid 
• 113100-53-1 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid 
• 676236-50-3 (1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)methanol 

Relevant academic research and scientific papers

Mechanistic Insight into Copper-Mediated Trifluoromethylation of Aryl Halides: The Role of CuI

The synthesis, characterization, and reactivity of key intermediates [Cu(CF3)(X)]-Q+ (X = CF3 or I, Q = PPh4) in copper-mediated trifluoromethylation of aryl halides were studied. Qualitative and quantitative studies showed [Cu(CF3)2]-Q+ and [Cu(CF3)(I)]-Q+ were not highly reactive. Instead, a much more reactive species, ligandless [CuCF3] or DMF-ligated species [(DMF)CuCF3], was generated in the presence of excess CuI. On the basis of these results, a general mechanistic map for CuI-promoted trifluoromethylation of aryl halides was proposed. Furthermore, on the basis of this mechanistic understanding, a HOAc-promoted protocol for trifluoromethylation of aryl halides with [Ph4P]+[Cu(CF3)2]- was developed.

PRODUCING METHOD FOR 3-DIFLUOROMETHYLPYRAZOLE COMPOUND, PRODUCING METHOD FOR 3-DIFLUOROMETHYLPYRAZOLE-4-CARBOXYLIC ACID COMPOUND, AND PYRAZOLIDINE COMPOUND

Provided are producing methods for a 3-difluoromethylpyrazole compound and a 3-difluoromethylpyrazole-4-carboxylic acid compound, which include, in a reaction solvent containing a specific solvent, subjecting a difluoroacetyl group-containing compound, a hydrazine compound, and formaldehyde to a cyclocondensation reaction, and subsequently oxidizing the obtained pyrazole compound precursor, and a pyrazolidine compound represented by a specific formula in these producing methods.

1 - Substituted - 5 - trifluoromethyl - 4 - the pyrazole is joint 1, 3, 4 - oxadiazole thioether or sulfones derivatives and use thereof

The invention discloses a kind of 1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole thioether or sulfone derivatives and application of the derivatives. The derivatives have the structures represented by general formulae A and B shown in the specification. 1-substituted-5-trifluoromethyl-4-pyrazol-1,3,4-oxadiazole compounds are synthesized from ethyl trifluoroacetoacetate by the following five reactions: esterification, ring closure, hydrazinolysis, ring closure and substitution. The compounds have certain inhibition effects to plant bacterial diseases or plant fungous diseases and can be used as pesticides and pesticide additives for preventing and controlling the plant bacterial diseases or the plant fungous diseases.

COMPOUNDS USEFUL AS CSF1 MODULATORS

This invention relates to novel compounds and to pharmaceutical compositions comprising the novel compounds. More specifically, the invention relates to compounds useful as Colony Stimulating Factor 1 Receptor (cFMS) modulators (e.g. cFMS inhibitors). This invention also relates to processes for preparing the compounds, uses of the compounds in treatment and methods of treatment employing the compounds. Specifically, the invention relates to the use of the compounds for the treatment of cancer and autoimmune diseases.

METHOD FOR PRODUCING 1-SUBSTITUTED-3-FLUOROALKYLPYRAZOLE-4-CARBOXYLIC ACID ESTER

The present invention is a method for producing a 1-substituted-3-fluoroalkylpyrazole-4-caroxylic acid ester, the method comprising a step of adding, to a first reaction liquid containing an alkyl hydrazine and a first organic solvent, a second reaction liquid containing an acyl acetic acid ester derivative and a second organic solvent in 0.5 to 30 hours to react the first reaction liquid with the second reaction liquid at a reaction temperature of -5 to 80°C under stirring in the absence of a base and an acid, wherein the first organic solvent and the second organic solvent are each at least any one of benzene, toluene, xylene, chlorobenzene, dichlorobenzene, ethyl acetate, butyl acetate, and dimethyl carbonate, a total mass of the first organic solvent and the second organic solvent is 1 to 60 times a mass of the acyl acetic acid ester derivative, and an amount of the first organic solvent in a total amount of the first organic solvent and the second organic solvent is 40 to 95% by mass.

PROCESS FOR THE REGIOSELECTIVE SYNTHESIS OF PYRAZOLES

A process is described for the synthesis of pyrazoles having general formula (I) which comprises the steps of mixing a compound having general formula (II) and a 1,2-disubstituted hydrazine having general formula (III) to form a reaction intermediate having general formula (IV) and the reaction mixture obtained in step i), in an acid environment, cyclizes to form a pyrazole having general formula (I), according to reaction scheme 1 Scheme 1.

Synthesis of 4-fluoromethylsydnones and their participation in alkyne cycloaddition reactions

We report the synthesis and some structural studies of 4-trifluoromethyl, 4-difluoromethyl-, and 4-monofluoromethylsydnones. All but the latter compounds are stable and represent effective precursors to a range of pyrazoles after cycloaddition reactions with alkynes. The cycloadditions are generally highly regioselective and provide 5-fluoromethylpyrazole products, although we have observed that Bn-substituted sydnones can provide an unexpected alkyne insertion mode that generates the 3-fluoromethyl isomer.

SUBSTITUTED BICYCLOCARBOXYAMIDE COMPOUNDS

This invention provides a compound of the formula (I). These compounds are useful for the treatment of disease conditions caused by overactivation of the VR1 receptor such as pain, or the like in mammal. This invention also provides a pharmaceutical composition comprising the above compound.

METHOD FOR PRODUCING 1-SUBSTITUTED-3-FLUOROALKYL PYRAZOLE-4-CARBOXYLATE

In a process for producing 1-substituted-3-fluoroalkyl-pyrazole-4-carboxylate (3) by a reaction of 2-alkoxymethylenefluoroacylacetate (1) and hydrazine (2), the reaction is conducted in the presence of a base and water, to produce 1-substituted-3-fluoroalkylpyrazole-4-carboxylate (3) with high selectivity and yield. This novel process enables to produce 1-substituted-3-fluoroalkylpyrazole-4-carboxylate (3), which is useful as an intermediate for pharmaceuticals and agrochemicals, with high selectivity and yield by simple and safe operations.

METHOD FOR PRODUCING 1-SUBSTITUTED-3-FLUOROALKYL PYRAZOLE-4-CARBOXYLATE

Disclosed is a method for producing 1-substituted-3-fluoroalkyl pyrazole-4-carboxylate (3) through a reaction between 2-alkoxymethylene fluoroacyl acetate (1) and a hydrazine (2). By performing the reaction in the presence of a base and water, 1-substituted-3-fluoroalkyl pyrazole-4- carboxylate (3) can be highly selectively produced with high yield. This novel method enables to highly selectively produce 1-substituted-3-fluoroalkyl pyrazole-4- carboxylate (3), which is useful as an intermediate for pharmaceutical and agrichemical products, with high yield by simple and safe operations.