775304-60-4

Basic information

• Product Name: Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester
• Synonyms: Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester;Methyl 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoate;3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-Benzoic acid Methyl ester;Ataluren impurity C
• CAS NO: 775304-60-4
• Molecular Formula: C₁₆H₁₁FN₂O₃
• Molecular Weight: 298.2685432
• Mol File: 775304-60-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester(775304-60-4)
• EPA Substance Registry System: Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester(775304-60-4)

Safety Data

• Hazardous Substances Data: 775304-60-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs with unique therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, this compound serves as an intermediate in the production of agrochemicals, potentially enhancing the effectiveness of pesticides and other agricultural chemicals.
Used in Fine Chemicals Synthesis:
Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester is utilized in the synthesis of fine chemicals, where its distinctive structure can be leveraged to create specialty chemicals for various applications.
Used in Medicinal Chemistry Research:
As a building block in medicinal chemistry, this ester is employed in research to explore its potential biological activities and to design new molecules with therapeutic relevance, contributing to the advancement of drug discovery.

Upstream product

• 775304-80-8 3-(N-2-fluorobenzoylcarbamimidoyl)-benzoic acid methyl ester 
• 912461-75-7 3-(N-2-fluorobenzoylamidino)benzoic acid methyl ester 
• 1141475-82-2 3-(N-hydroxycarbamimidoyl)-benzoic acid methyl ester 
• 393-52-2 2-Fluorobenzoyl chloride 
• 1877-72-1 3-Cyanobenzoic acid 
• 13531-48-1 methyl 3-cyanobenzoate 
• 15676-11-6 3-(carbamimidoyl)benzoic acid methyl ester 
• 344412-41-5 methyl 3-((hydroxyimino)methyl)benzoate 
• 394-47-8 2-fluorobenzonitrile 
• 52178-50-4 Methyl 3-formylbenzoate 
• 619-21-6 m-formylphenyl benzoic acid 
• 1141475-82-2 3-(N-hydroxyamidino)benzoic acid methyl ester 
• 67-56-1 methanol 
• 775304-57-9 ataluren 

Downstream Products

• 775304-57-9 ataluren 

Relevant articles and documents

Preparation method of Ataluren

The invention discloses a preparation method of Ataluren. The preparation method comprises an addition step in which under an alkaline condition, 3-cyanobenzoate reacts with hydroxylamine hydrochloride by using a first mixed solvent to obtain an intermediate as shown in a formula III, a condensation step in which in a first organic solvent, a condensation reaction is conducted on the intermediate shown in the formula III and o-fluorobenzoic acid to obtain an intermediate shown in a formula IV, a cyclization step in which in a second organic solvent, catalyzing is conducted by using Lewis acid, and intramolecular dehydration is conducted on the intermediate in the formula IV to obtain an intermediate in a formula V, and an ester hydrolysis step in which under an alkaline condition, ester hydrolysis is conducted on the intermediate in the formula V by using a second mixed solvent to obtain the product. Cheap raw materials are subjected to addition, condensation, cyclization and ester hydrolysis, the reaction conditions are mild, the process is simple, the cost is low, and industrial production is facilitated. Meanwhile, the solvent in the reaction process can be basically recycled, the synthesis cost is low, and the reaction environment is good; in addition, the purification operation is simple, and the total yield and the product purity of the target compound Ataluren are high.

Method for preparing ataluren

The invention discloses a method for preparing ataluren, (PTC124, a commodity name of ataluren) and belongs to the field of organic synthesis. The preparation method comprises the following steps: (1)reacting methyl m-cyanobenzoate with hydroxylamine hydrochloride in a lower alcohol or a mixed solvent of a lower alcohol and water to generate 3-(N-hydroxyamidino)-methyl benzoate; (2) carrying outO-acylation reaction between the 3-(N-hydroxyamidino)-methyl benzoate and o-fluorobenzoyl chloride in an organic solvent to obtain 3-((5-(2-fluorophenyl))-3-(1,2,4-oxadiazolyl)-methyl benzoate; (3) under the catalytic action of tetra-alkyl ammonium halide, carrying out cyclization to obtain 3-((5-(2-fluorophenyl))-3-(1,2,4-oxadiazolyl)-methyl benzoate; and (4) hydrolyzing to obtain ataluren. The synthesis method is a simple and efficient synthesis method of ataluren.

Potassium Poly(Heptazine Imide): Transition Metal-Free Solid-State Triplet Sensitizer in Cascade Energy Transfer and [3+2]-cycloadditions

Polymeric carbon nitride materials have been used in numerous light-to-energy conversion applications ranging from photocatalysis to optoelectronics. For a new application and modelling, we first refined the crystal structure of potassium poly(heptazine imide) (K-PHI)—a benchmark carbon nitride material in photocatalysis—by means of X-ray powder diffraction and transmission electron microscopy. Using the crystal structure of K-PHI, periodic DFT calculations were performed to calculate the density-of-states (DOS) and localize intra band states (IBS). IBS were found to be responsible for the enhanced K-PHI absorption in the near IR region, to serve as electron traps, and to be useful in energy transfer reactions. Once excited with visible light, carbon nitrides, in addition to the direct recombination, can also undergo singlet–triplet intersystem crossing. We utilized the K-PHI centered triplet excited states to trigger a cascade of energy transfer reactions and, in turn, to sensitize, for example, singlet oxygen (1O2) as a starting point to synthesis up to 25 different N-rich heterocycles.

A Direct Approach to Decoration of Bioactive Compounds via C-H Amination Reaction

The development of new methods to achieve the direct synthesis of bioactive organic molecules is always an important topic in organic synthesis. We hereby demonstrate that N-methoxyamide is an excellent amino source in the iridium-catalyzed intermolecular C-H amination reaction. The linkage of two bioactive organic molecules can be well achieved with this new protocol. More than 20 examples of decorated bioactive compounds were reported, which can facilitate the discovery of new bioactive molecules.

Metal-Catalyzed Synthesis of Functionalized 1,2,4-Oxadiazoles from Silyl Nitronates and Nitriles

The metal-catalyzed cycloaddition of silyl nitronates and nitriles leading to 1,2,4-oxadiazoles is described. Silver(I) triflate (AgOTf) and and ytterbium(III) triflate [Yb(OTf)3] are suitable catalysts. A variety of functional groups is tolerated in the nitrile. The reaction works well for alkenyl and aryl silyl nitronates while the use of alkyl silyl nitronates is less efficient. Mechanistic studies are in favour of an elimination of tert-butyl(dimethyl)silanol (TBSOH) after the cycloaddition step. The new approach has also been applied for the synthesis of the drug ataluren. (Figure presented.).

Palladium-Catalyzed, Silver-Assisted Direct C-5–H Arylation of 3-Substituted 1,2,4-Oxadiazoles under Microwave Irradiation

A direct C-5–H arylation of 3-substituted 1,2,4-oxadiazoles with aryl iodides in the presence of a palladium catalyst and silver acetate is reported. This method provides a rapid, reliable way to obtain versatile 3,5-diaryl-1,2,4-oxadiazole derivatives, which are common moieties of many biologically active molecules. The synthetic applications of this novel method have been demonstrated in the concise syntheses of Ataluren and a potent RET inhibitor Yhhu251. (Figure presented.).

Oxdiazole compound solvate and preparation method thereof

The present invention relates to the dimethyl sulfoxide solvate of 3-[5-(2-fluorophenyl)-[1,2,4]oxdiazole-3-yl]benzoic acid, wherein the dimethyl sulfoxide solvate has characteristics of good stability, high purity, excellent particle and excellent shape, and is suitable for pharmaceutical preparation applications. The present invention further relates to a preparation method of the dimethyl sulfoxide solvate, a pharmaceutical composition of the dimethyl sulfoxide solvate, and uses of the dimethyl sulfoxide solvate in preparation of drugs for treatment of genetic diseases.

Enhancement of premature stop codon readthrough in the CFTR gene by Ataluren (PTC124) derivatives

Abstract Premature stop codons are the result of nonsense mutations occurring within the coding sequence of a gene. These mutations lead to the synthesis of a truncated protein and are responsible for several genetic diseases. A potential pharmacological

Bis-aryloxadiazoles as effective activators of the aryl hydrocarbon receptor

Bis-aryloxadiazoles are common scaffolds in medicinal chemistry due to their wide range of biological activities. Previously, we identified a 1,2,4-bis-aryloxadiazole that blocks mammary branching morphogenesis through activation of the aryl hydrocarbon receptor (AHR). In addition to defects in mammary differentiation, AHR stimulation induces toxicity in many other tissues. We performed a structure activity relationship (SAR) study of 1,2,4-bis-aryloxadiazole to determine which moieties of the molecule are critical for AHR activation. We validated our results with a functional biological assay, using desmosome formation during mammary morphogenesis to indicate AHR activity. These findings will aid the design of oxadiazole derivative therapeutics with reduced off-target toxicity profiles.

PROCESSES FOR THE PREPARATION OF 1,2,4-OXADIAZOLE BENZOIC ACIDS

Provided herein are processes for the preparation of compounds useful for the treatment, prevention or management of diseases associated with a nonsense mutation. More specifically, provided herein are processes for the synthesis of 1,2,4-oxadiazoles. In particular, provided herein are processes useful for the preparation of 3-[5-(2-fluorophenyl)- [1,2,4]oxadiazol-3-yl]-benzoic acid.