785-74-0

Usage

Uses

Used in Research and Development:
3-OXO-N-(3-(TRIFLUOROMETHYL)PHENYL)BUTANAMIDE is used as a building block for the synthesis of other chemical compounds, contributing to the advancement of chemical research and the creation of new materials.
Used in Medicinal and Pharmaceutical Industries:
In the medicinal and pharmaceutical industries, 3-OXO-N-(3-(TRIFLUOROMETHYL)PHENYL)BUTANAMIDE is used for its potential therapeutic properties. It has been studied for its anti-inflammatory and analgesic effects, which could make it a valuable compound for treating various medical conditions.

InChI:InChI=1/C11H10F3NO2/c1-7(16)5-10(17)15-9-4-2-3-8(6-9)11(12,13)14/h2-4,6H,5H2,1H3,(H,15,17)

Upstream product

• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 98-16-8 3-trifluoromethylaniline 
• 1694-31-1 tert-butyl acetoacetate 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 141-97-9 ethyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 64129-59-5 3-methyl-3'-trifluoromethyl-5,6-dihydro-4H-imidazo-[2,1-b] thiazole-2-carboxanilide hydrochloride 
• 1588498-98-9 C₁₅H₁₆F₃NO₂ 
• 463342-69-0 (1Z)-2-oxo-N-phenyl-2-{[3-(trifluoromethyl)phenyl]amino}ethanehydrazonoyl chloride 
• 106878-54-0 2-chloro-3-oxo-N-[3-(trifluoromethyl)phenyl]butanamide 
• 61643-55-8 2-[1-Ethoxy-meth-(Z)-ylidene]-3-oxo-N-(3-trifluoromethyl-phenyl)-butyramide 
• 3870-70-0 2,4-di-acetyl-α,α,α,α',α',α'-hexafluoro-m-glutarotoluidide 

Relevant academic research and scientific papers

Palladium-Catalyzed Regioselective Coupling Cyclohexenone into Indoles: Atom-Economic Synthesis of β-Indolyl Cyclohexenones and Derivatization Applications

Herein, we report a palladium-catalyzed dehydrogenative cross-coupling of indoles with cyclic enones to give β-indolyl cyclic enones under mild and neutral reaction conditions. The key to the success is to explore a mild condition, which ensures the indole C-H activation and subsequent syn β-hydride elimination through rapid enolization isomerization of Pd(II)-enolate while suppressing other undesired side reactions. Synthetic utility has also been demonstrated in the flexible transformation of the coupling products to meta-phenols and benzo[a]carbazoles.

An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space

The present study describes the preparation of N-aryl-(15) and N-alkyl-(17) acetoacetamides, in good to excellent yields, using both conventional and microwave heating, by reaction of amine derivatives (14 and 16) with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD, 12) in aqueous medium. The acetoacetamides were used to prepare novel Biginelli dihydropyrimidine derivatives. The introduction of the amino acid derivatives potentially allows for the exploration of new structural complexity and topologically diversifies the chemical space occupied by this versatile chemical scaffold.

Ligand-enabled γ-C-H olefination and carbonylation: Construction of β-quaternary carbon centers

Monoselective γ-C-H olefination and carbonylation of aliphatic acids has been accomplished by using a combination of a quinoline-based ligand and a weakly coordinating amide directing group. The reaction provides a new route for constructing richly functionalized all-carbon quaternary carbon centers at the β-position of aliphatic acids.

On the Knorr synthesis of 6-bromo-4-methylquinolin-2(1H)-one

In the course of our work on infectious diseases, we were led to prepare 6-bromo-2-chloro-4-methylquinoline as a starting material. Since surprisingly little has been reported in the literature, the two synthetic steps to this compound were investigated. The synthesis involves a condensation between -keto esters and 4-bromoaniline and the cyclization of the resulting anilides into 6-bromoquinolin-2(1H)-one, otherwise known as the Knorr reaction. The 1H NMR monitoring of the first step allowed us to optimize the conditions leading specifically to the anilide without the occurrence of the alternative crotonate. To illustrate the scope of our finding, few additional anilides featuring electron-attracting groups were prepared. The study of their cyclization revealed some unsuspected steric effect governing this second step. Aside from rectifying a few claims in this chemistry, this study led to a three-step preparation of 6-bromo-2-chloro-4-methylquinoline in 48% overall yield from 4-bromoaniline. Georg Thieme Verlag Stuttgart - New York.

Structure elucidation of N-aryl-2-chloro-3-oxobutanamides with respect to intra- and intermolecular hydrogen bonding

In general, N-aryl-2-chloro-3-oxobutanamides form in solid state an intermolecular hydrogen bond between the anilide hydrogen and the anilide carbonyl oxygen of a neighbouring molecule, which is disrupted in solution. An intramolecular association could not be detected.

Synthesis and structural assignment of oxanilo-N-arylhydrazonoyl chlorides

Oxanilo-N-arylhydrazonoyl chlorides have been prepared from appropriate N-aryl-2-chloro-3-oxobutanamides by the Japp-Klingemann reaction. The structures of the title compounds have been established in the solid state by single-crystal X-ray structure determination and IR spectroscopy, and in solution by IR, UV, and 1H and 13C NMR spectroscopy. The results indicate that the hydrazonoyl chloride moiety adopts the (Z)-configured form. In the crystal, intramolecular hydrogen bonds generally exist between the chloride function and the hydrazone hydrogen atom, and also between the amide hydrogen atom and the double-bonded nitrogen atom of the hydrazone moiety. In solution, this intramolecular hydrogen bonding could not be detected. In compounds with an ortho-chloro-substituted NH-aryl moiety, however, the chlorine atom is involved in hydrogen bonding to the NH hydrogen atom both in the crystal and in solution. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthesis and immunosuppressant activity of pyrazole carboxamides

A series of novel pyrazole carboxamides sis disclosed that demonstrate strong immunosuppressant activity in rodent and human mixed leukocyte response (MLR) assays (IC50 1 μM). The synthesis, biological activity, mode of action, and pharmacokinetic properties of this new lead series are discussed.

4-isoxazolecarboxamide derivatives

This invention is directed to compounds of the formula (I): STR1 wherein R1 is --OR4 (where R4 is hydrogen, lower alkyl, lower hydroxyalkyl, phenyl, phenyl-lower-alkyl, or --(CH2)n Y where n is an integer from 1 to 4 and Y is morpholino, -SR5, --C(O)OR5, --C(O)N(R6)2, --N(R6)2, or --N+ (R6)3 X-, in which R5 is lower alkyl, each R6 is independently selected from hydrogen or lower alkyl, and X is halogen) or --SR7 (where R7 is lower alkyl, phenyl-lower-alkyl, or --(CH2)n W where W is --N(R6)2 or --N+ (R6)3 X-, and n, R6 and X are as previously defined); R2 is lower alkyl, phenyl or phenyl-lower-alkyl; R3 is halo, hydroxy, lower alkyl, lower alkoxy, lower haloalkyl, lower haloalkoxy, or --C(O)OR5 where R5 is as previously defined; and Z is a bond, 2,5-thienyl or 2,5-furanyl; or a pharmaceutically acceptable salt thereof. These compounds are useful in treating inflammation, autoimmune disease or allograft rejection in mammals.

Effect of Structural Change on Acute Toxicity and Antiinflammatory Activity in a Series of Imidazothiazoles and Thiazolobenzimidazoles

The effect of structural change on the biological activity of a series of imidazothiazoles and thiazolobenzimidazoles is described.It was found that compounds with polar substituents at the 2 or 3 position of the ring system are less acutely toxic while maintaining antiinflammatory activity.Other structural changes, such as the incorporation of a gem-dimethyl substituent in the 6 position, increase acute toxicity and eliminate antiinflammatory activity.The compound with the best activity/toxicity ratio contains an alkyl sulfonyl substituent on the thiazole ring.The thiazolobenzimidazole analogues are more potent than the imidazole analogues.

2-Acylaminothiazol-4-ylacetamides as post-emergent selective herbicides

A class of amides disclosed to be useful as selective post-emergent herbicides are those having the general structural formula STR1 in which R1 is hydrogen or lower alkyl, R2 is amino, lower alkyl, lower chloroalkyl, lower alkylamino, lower alkenylamino, lower alkoxy or C3 to C5 cycloalkyl and R3 is phenyl, thiazolyl, thiadiazolyl or lower alkyl-substituted, halogen-substituted or trifluoromethyl-substituted phenyl, thiazolyl or thiadiazolyl.