351-87-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Trifluoromethylaceto-acetanilide is used as an intermediate for the synthesis of pharmaceutical drugs due to its ability to contribute to the development of biologically active molecules. Its presence in the synthesis process aids in creating compounds with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, 4-Trifluoromethylaceto-acetanilide serves as a crucial intermediate, facilitating the production of various agrochemicals that are essential for crop protection and enhancement of agricultural yields.
Used in Organic Synthesis:
4-Trifluoromethylaceto-acetanilide is utilized as a building block in organic synthesis, allowing for the creation of a wide array of synthetic organic compounds that can be applied across different industries.
Used in Research and Development:
4-Trifluoromethylaceto-acetanilide is used as a subject of research for its potential anti-inflammatory, analgesic, and anticancer properties, indicating its importance in the discovery and development of new medications and therapies.

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

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 455-14-1 4-trifluoromethylphenylamine 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 1694-31-1 tert-butyl acetoacetate 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 1206724-43-7 2-bromo-3-oxo-N-[4-(trifluoromethyl)phenyl]butanamide 
• 1241917-16-7 6-methyl-2-oxo-4-phenyl-N-[4-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carboxamide 
• 1258407-68-9 4-(furan-2-yl)-6-methyl-N-(4-trifluoromethylphenyl)-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 1258407-64-5 4-(thiophen-2-yl)-6-methyl-N-(4-trifluoromethylphenyl)-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 1258407-56-5 4-phenyl-6-methyl-N-(4-trifluoromethylphenyl)-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 1448691-80-2 4-hydroxy-4-methyl-2-(4-(trifluoromethyl)phenyl)-2-azaspiro[4.4]nonan-1-one 
• 1448692-13-4 C₁₅H₁₆F₃NO₂ 
• 163451-81-8 teriflunomide 
• 75706-12-6 Leflunomide 

Relevant academic research and scientific papers

Preparation method of 3-oxo-N-(4-trifluoromethylphenyl) butylamide

The invention relates to a preparation method of 3-oxo-N-(4-trifluoromethylphenyl) butylamide, wherein the preparation method comprises the steps: carrying out amidation reaction on ethyl acetoacetateand p-trifluoromethylaniline to obtain 3-oxo-N-(4-trifluoromethylphenyl) butylamide, wherein in the reaction process, excessive p-trifluoromethylaniline is used as a solvent, and a catalyst adopted in the reaction process is an organic base catalyst. Compared with the prior art, the preparation method has the advantages that ethyl acetoacetate and p-trifluoromethylaniline are subjected to amidation reaction, and the product 3-oxo-N-(4-trifluoromethylphenyl) butylamide is obtained through post-treatment, wherein the synthesis operation of the 3-oxo-N-(4-trifluoromethylphenyl) butylamide is simple, the cost is low, the yield is high, the use of volatile toxic organic solvents and the emission of waste gas are avoided, and the process route is green and environment-friendly; and the obtainedproduct has few impurities, the target product has high purity, the raw materials are easy to recycle, the post-treatment operation is simple, the reaction time is shortened, and the method is suitable for industrial production.

Nickel-promoted oxidative domino Csp3-H/N-H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones

The first nickel-catalyzed oxidative domino Csp3-H/N-H double isocyanide insertion reaction of acetamides with isocyanides has been developed for the synthesis of pyrrolin-2-one derivatives. A wide range of acetamides bearing various functional groups are compatible with this reaction system by utilizing Ni(acac)2as a catalyst. In this transformation, isocyanide could serve as a C1 connector and insert into the inactive Csp3-H bond, representing an effective way to construct heterocycles.

HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst

A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.

5-Aminothiophene-2,4-dicarboxamide analogues as hepatitis B virus capsid assembly effectors

Chronic hepatitis B virus (HBV) infection represents a major health threat. Current FDA-approved drugs do not cure HBV. Targeting HBV core protein (Cp) provides an attractive approach toward HBV inhibition and possibly infection cure. We have previously identified and characterized a 5-amino-3-methylthiophene-2,4-dicarboxamide (ATDC) compound as a structurally novel hit for capsid assembly effectors (CAEs). We report herein hit validation through studies on absorption, distribution, metabolism and excretion (ADME) properties and pharmacokinetics (PK), and hit optimization via analogue synthesis aiming to probe the structure-activity relationship (SAR) and structure-property relationship (SPR). In the end, these medicinal chemistry efforts led to the identification of multiple analogues strongly binding to Cp, potently inhibiting HBV replication in nanomolar range without cytotoxicity, and exhibiting good oral bioavailability (F). Two of our analogues, 19o (EC50 = 0.11 μM, CC50 > 100 μM, F = 25%) and 19k (EC50 = 0.31 μM, CC50 > 100 μM, F = 46%), displayed overall lead profiles superior to reported CAEs 7–10 used in our studies.

Chemical and structural studies provide a mechanistic basis for recognition of the MYC G-quadruplex

G-quadruplexes (G4s) are noncanonical DNA structures that frequently occur in the promoter regions of oncogenes, such as MYC, and regulate gene expression. Although G4s are attractive therapeutic targets, ligands capable of discriminating between differen

Silver(I)-catalyzed tandem approach to β-oxo amides

A facile and efficient AgI-catalytic approach is reported for the first time to synthesize β-oxo amides from β-oxo esters a with broad substrate scope in good to excellent yields. Crossover and in situ NMR studies confirmed that the reaction occurred through a new pathway and not by the traditional condensation reaction. The key advantages of this method are the readily available starting materials, the air-stable reaction, the simple protocol, and the environmental friendliness. A new, catalytic approach to the synthesis of β-oxo amides from β-oxo esters with a broad substrate scope in good to excellent yields was developed. In situ NMR spectroscopy and crossover experiments confirmed the reaction mechanism.

Multicomponent strategy to indeno[2,1- C ]pyridine and hydroisoquinoline derivatives through cleavage of carbon-carbon bond

A concise and efficient three-component domino reaction has been developed for the synthesis of polyfunctionalized indenopyridine and hydroisoquinoline derivatives via the cleavage of a C-C bond under transition-metal-free conditions. This reaction provides facile access to complex nitrogen-containing heterocycles by simply mixing three common starting materials in EtOH in the presence of 20 mol % NaOH under microwave irradiation conditions.

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.

A PROCESS FOR THE PREPARATION OF TERIFLUNOMIDE

The present invention provides a process for preparing Teriflunomide of formula (I).