1088994-22-2

Usage

Uses

Used in Pharmaceutical Industry:
5-methyl-2-(pyrimidin-2-yl)benzoic acid is used as a building block for the synthesis of various pharmaceuticals due to its chemical structure, which may confer specific biological activities. It is particularly valuable in drug discovery and development, where its unique molecular features can be leveraged to create new therapeutic agents.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 5-methyl-2-(pyrimidin-2-yl)benzoic acid serves as a key component in the synthesis of a wide range of organic compounds. Its versatile structure allows for the creation of diverse chemical entities with potential applications in various industries.
Used in Dyes and Pigments Production:
5-methyl-2-(pyrimidin-2-yl)benzoic acid is utilized in the production of dyes and pigments, capitalizing on its chemical properties to create colorants for various applications, including textiles, plastics, and printing inks.
Used in Medicinal Chemistry Research:
As a potential candidate for drug design, 5-methyl-2-(pyrimidin-2-yl)benzoic acid is employed in medicinal chemistry research to explore its biological activities and evaluate its potential as a precursor for the development of new pharmaceutical agents. Its unique structural features make it an interesting subject for study in the quest to discover novel therapeutic compounds.

Upstream product

• 1722-12-9 2-chloropyrimidine 
• 6967-82-4 2-bromo-5-methylbenzoic acid 
• 1373917-20-4 5-methyl-2-pyrimidin-2-ylbenzonitrile 
• 42872-83-3 2-bromo-5-methylbenzylnitrile 
• 1088994-18-6 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester 
• 103440-52-4 methyl 2-iodo-5-methylbenzoate 
• 52548-14-8 2-iodoyl-5-methylbenzoic acid 
• 1088994-20-0 5-methyl-2-(pyrimidin-2-yl)benzoic acid methyl ester 

Downstream Products

• 1088991-73-4 MK-6096 
• 1260527-48-7 (+/-)-(5-((5-chloropyridin-2-ylamino)methyl)-6-azaspiro[2.5]octan-6-yl)(5-methyl-2-(pyrimidin-2-yl)phenyl)methanone 
• 1381971-14-7 N-ethyl-N-{2-[3-(5-fluoropyridin-2-yl)-1H-pyrazol-1-yl]ethyl}-5-methyl-2-(pyrimidin-2-yl)benzamide 
• 1384261-53-3 (1R,4R,6R)-3-{[5-methyl-2-(2-pyrimidinyl)phenyl]carbonyl}-4-{2-[5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-azabicyclo[4.1.0]heptane 
• 1295516-46-9 (1R,6S)-[8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-(5-methyl-2-pyrimidin-2-yl-phenyl)-methanone 
• 1262396-05-3 (6(S)-(((5-chloropyridin-2-yl)amino)methyl)-5-azaspiro[2.4]heptan-5-yl)(5-methyl-2-(pyrimidin-2-yl)phenyl)methanone 

Relevant academic research and scientific papers

Condition optimization for synthesis of 5-methyl-2(Pyrimidin-2-yl) benzoic acid

Orexin has been emerged as a hot and frontier research theme in the close relationship with sleep-wake regulation. In this paper, we report a synthetic method for the preparation of 5-methyl-2-(pyrimidin-2-yl)benzoic acid, which is an important molecular fragment of orexin Filorexant (MK-6096). Compared to the previously reported methods, the current route has the advantages of a short synthetic pathway, simple post-treatment, and high yield that provide an effective new methodology for the synthesis of the target compound. Using 2-bromo-5-methyl benzoic acid and 2-chloropyrimidine as raw materials, PdCl2(PPh3)2 is used as a metal catalyst to mediate one-pot genera-tion of 5-methyl-2-(pyrimidin-2-yl)benzoic acid using the Negishi cross-coupling method. The optimum condition involves 2-bromo-5-methylbenzoic acid (10.00 g) and anhydrous zinc chloride powder (6.32 g) together with the catalyst: 2-bromo-5-methylbenzoic acid molar ratio of 0.02 and 2-chloropyrimidine: 2-bromo-5-methylbenzoic acid molar ratio of 1.1:1 at a reaction temperature of 55°C for 14 h. Under these optimum reaction conditions, the maximum yield of 78.4% is attained for 5-methyl-2-(pyrimidin-2-yl) benzoic acid.

Crystal form of orexin receptor antagonist compound, and preparation method and application thereof

Disclosed are a preparation method of an orexin receptor antagonist compound 5-3, Crystalline forms I-IV of an orexin receptor antagonist compound 5-3 are provided. Also provided are processes of the preparing the orexin receptor antagonist compound 5-3 a

SUBSTITUTED 2-AZABICYCLO[3.1.1]HEPTANE AND 2-AZABICYCLO[3.2.1]OCTANE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS

There is provided a compound of formula (I), wherein L1 to L3, R1 to R4, X, A and B have meanings given in the description, and pharmaceutically acceptable salts, solvates and prodrugs thereof, which compounds are useful as antagonists of the orexin-1 and orexin-2 receptors or as selective antagonists of the orexin-1 receptor, and thus, in particular, in the treatment or prevention of inter alia substance dependence, addiction, anxiety disorders, panic disorders, binge eating, compulsive disorders, impulse control disorders, cognitive impairment and Alzheimer's disease.

Substituted heterocyclic compound, and use method and use thereof

The invention relates to a substituted heterocyclic compound, and a use method and a use thereof. The substituted heterocyclic compound and a medicinal composition including the compound can be used to depress orexin receptors, especially an orexin-1 rece

USE OF BENZIMIDAZOLE-PROLINE DERIVATIVES

The present invention relates to compounds of the formula (I), wherein Ar1 and Ar2 are as described in the description and to their use as pharmaceuticals for the treatment of sundown syndrome. The invention also relates to the preparation of such compounds and of pharmaceutically acceptable salts thereof.

Unusual pyrimidine participation: Efficient stereoselective synthesis of potent dual orexin receptor antagonist MK-6096

An asymmetric synthesis of dual orexin receptor antagonist MK-6096 (1) is described. Key steps for the trans-2,5-disubstituted piperidinyl ether fragment include a biocatalytic transamination, a trans-selective Mukaiyama aldol, and a regioselective pyridy

Convergent kilogram-scale synthesis of dual orexin receptor antagonist

MK-6096 is an orexin receptor antagonist in clinical trials for the treatment of insomnia. Herein we describe its first kilogram-scale synthesis. Chirality on the α-methylpiperidine core was introduced in a biocatalytic transamination using a three-enzyme system with excellent enantioselectivity (>99% ee). Low diastereoselectivity of the lactam reduction was overcome by development of a camphor sulfonic acid salt formation and dr upgrade. A chemoselective O-alkylation with 5-fluoro-2-hydroxypyridine was optimized and developed. Overall, 1.2 kg of MK-6069 was prepared in nine steps and 13% overall yield.

PROCESS FOR THE PREPARATION OF AN OREXIN RECEPTOR ANTAGONIST

The present invention is directed to processes for preparing a pyridyl piperidine compound which is an antagonist of orexin receptors, and which is useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexi

PROCESS FOR THE PREPARATION OF AN OREXIN RECEPTOR ANTAGONIST

The present invention is directed to processes for preparing a pyridyl piperidine compound which is an antagonist of orexin receptors, and which is useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved.

PYRIDYL PIPERIDINE OREXIN RECEPTOR ANTAGONISTS

The present invention is. directed to pyridyl piperidine compounds of formula (I) which are antagonists of orexin receptors, and which are useful' in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which orexin receptors are involved.