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Usage

Uses

Used in Organic Chemistry Research:
5-Methyl-2-(1H-1,2,3-triazol-1-yl)benzoic acid is used as a research compound for its unique structure and properties. It is valuable in the study of organic chemistry due to the presence of different functional groups, which can be utilized in various chemical reactions and synthesis processes.
Used in Pharmaceutical Development:
Although its exact physical properties, toxicity, and uses in industrial applications have not been extensively studied, 5-Methyl-2-(1H-1,2,3-triazol-1-yl)benzoic acid holds potential for pharmaceutical development. Its unique structure may contribute to the discovery of new drug candidates or the improvement of existing ones, particularly in the area of medicinal chemistry.
Used in Chemical Synthesis:
5-Methyl-2-(1H-1,2,3-triazol-1-yl)benzoic acid is used as a starting material or intermediate in the synthesis of more complex organic compounds. Its functional groups can be manipulated to produce a variety of derivatives, which can be further utilized in the development of new chemical products or materials.
Used in Material Science:
The potential applications of 5-Methyl-2-(1H-1,2,3-triazol-1-yl)benzoic acid in material science are currently being explored. Its unique structure and properties may contribute to the development of new materials with specific characteristics, such as improved stability, reactivity, or selectivity in various applications.

Upstream product

• 288-36-8 1,2,3-triazole 
• 52548-14-8 2-iodoyl-5-methylbenzoic acid 
• 6967-82-4 2-bromo-5-methylbenzoic acid 
• 288-36-8 1 ,2,3-Triazole 

Relevant academic research and scientific papers

Identification of ortho-Substituted Benzoic Acid/Ester Derivatives via the Gas-Phase Neighboring Group Participation Effect in (+)-ESI High Resolution Mass Spectrometry

Benzoic acid/ester/amide derivatives are common moieties in pharmaceutical compounds and present a challenge in positional isomer identification by traditional tandem mass spectrometric analysis. A method is presented for exploiting the gas-phase neighbor

SUBSTITUTED PROLINES / PIPERIDINES AS OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to compounds that can modulate the bioactivity of an orexin receptor such as OX1 or OX2, or both; to pharmaceutical compositions and combinations comprising a compound of the invention; to methods of treatment of malconditions in patients wherein modulation of an orexin receptor is medically indicated; and to methods of preparation of compounds of the invention.

2,5-DISUBSTITUTED THIOMORPHOLINE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to 2,5-disubstituted thiomorpholine amide compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the 2,5-disubstituted thiomorpholine amide compounds described herein in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to pharmaceutical compositions comprising these compounds. The present invention is also directed to uses of these pharmaceutical compositions in the prevention or treatment of such diseases in which orexin receptors are involved.

Enantioselective synthesis of a dual orexin receptor antagonist

A concise, enantioselective synthesis of the potent dual orexin inhibitor suvorexant (1) is reported. Key features of the synthesis include a mild copper-catalyzed amination, a highly chemoselective conjugate addition, and a tandem enantioselective transamination/seven-membered ring annulation. The synthesis requires inexpensive starting materials and only four linear steps for completion.

The first large-scale synthesis of MK-4305: A dual orexin receptor antagonist for the treatment of sleep disorder

A new synthetic route to drug candidate 1, a potent and selective dual orexin antagonist for the treatment of sleep disorders, has been developed. The key acyclic precursor 10 was prepared in a one-step process in 75% isolated yield from commercially available starting materials using novel chemistry to synthesize 2-substituted benzoxazoles. A reductive amination was followed by a classical resolution to afford chiral diazepane (R)-11. Finally, coupling of (R)-11 with acid 5 furnished the desired drug candidate 1.

Discovery of the dual orexin receptor antagonist [(7 R)-4-(5-chloro-1,3- benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl][5-methyl-2-(2 H -1,2,3-triazol-2-yl)phenyl]methanone (MK-4305) for the treatment of insomnia

Despite increased understanding of the biological basis for sleep control in the brain, few novel mechanisms for the treatment of insomnia have been identified in recent years. One notable exception is inhibition of the excitatory neuropeptides orexins A and B by design of orexin receptor antagonists. Herein, we describe how efforts to understand the origin of poor oral pharmacokinetics in a leading HTS-derived diazepane orexin receptor antagonist led to the identification of compound 10 with a 7-methyl substitution on the diazepane core. Though 10 displayed good potency, improved pharmacokinetics, and excellent in vivo efficacy, it formed reactive metabolites in microsomal incubations. A mechanistic hypothesis coupled with an in vitro assay to assess bioactivation led to replacement of the fluoroquinazoline ring of 10 with a chlorobenzoxazole to provide 3 (MK-4305), a potent dual orexin receptor antagonist that is currently being tested in phase III clinical trials for the treatment of primary insomnia.

2,5-DISUBSTITUTED PIPERIDINE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to 2,5-disubstituted piperidine amide compounds 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.

2,3-DISUBSTITUTED PIPERIDINE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to 2,3-disubstituted piperidine amide compounds 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 recepto

SUBSTITUTED DIAZEPAN OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to diazepan compounds which are antagonists of orexin receptors, and which are useful in the treatment 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 treatment of such diseases in which orexin receptors are involved.

SUBSTITUTED DIAZEPAN OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to substituted diazepan compounds 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.