76162-56-6

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Methyl-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester is used as a building block in the pharmaceutical industry for the synthesis of various drugs. Its nucleophilic nature allows it to participate in key reactions, contributing to the development of new medicinal compounds with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical sector, 3-Methyl-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester serves as an essential component in the creation of pesticides, herbicides, and other crop protection agents. Its reactivity in organic synthesis enables the production of effective and targeted agrochemicals that enhance crop yields and protect against pests.
Used in Organic Compounds Synthesis:
3-Methyl-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester is utilized as a versatile intermediate in the synthesis of a wide range of organic compounds. Its ability to engage in nucleophilic reactions and form carbon-carbon bonds makes it a valuable asset in the development of novel organic molecules for various applications, including materials science, chemical research, and specialty chemicals production.

Upstream product

• 54681-68-4 5-bromo-3-methyl-1,2,4-thiadiazole 
• 541-41-3 chloroformic acid ethyl ester 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 98026-50-7 5-iodo-3-methyl-1,2,4-thiadiazole 
• 17452-74-3 5-Methyl-1,3,4-oxathiazole-2-one 
• 623-49-4 ethyl cyanoformate 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 16982-21-1 ethyl 2-amino-2-thioxoacetate 

Downstream Products

• 1009621-29-7 (3-methyl-[1,2,4]thiadiazol-5-yl)-diphenyl-methanol 
• 1375066-73-1 3-methyl-1,2,4-thiadiazole-5-carbohydrazide 

Relevant academic research and scientific papers

SYNTHESIS OF 3-METHYL-1,2,4-THIADIAZOLE-5-CARBOHYDRAZIDE OR OF THE METHYL-d3 DEUTERATED FORM THEREOF

The present invention relates to a method of synthesis of compound (I), wherein R1 represents methyl or methyl-d3, thus corresponding to 3-methyl-1,2,4-thiadiazole-5-carbohydrazide or to the methyl-d3 deuterated form thereof. These compounds are useful as key intermediates in the synthesis of pharmaceutical compounds, especially fezolinetant and deuterated fezolinetant.

Microwave-induced generation and reactions of nitrile sulfides: An improved method for the synthesis of isothiazoles and 1,2,4-thiadiazoles

The 1,3-dipolar cycloaddition reactions of nitrile sulfides, generated by microwave-assisted decarboxylation of 1,3,4-oxathiazol-2-ones, have been investigated. By this approach ethyl 1,2,4-thiadiazole-5-carboxylates 3 were prepared in good yield by cycloaddition of the nitrile sulfides to ethyl cyanoformate. Similarly, reaction of benzonitrile sulfide with dimethyl acetylenedicarboxylate (DMAD) afforded dimethyl 3-phenylisothiazole-4,5- dicarboxylate (5). In contrast, o-hydroxybenzonitrile sulfide, generated from the corresponding oxathiazolone 2d, reacted with DMAD to give methyl 4-oxo-4H-[1]benzopyrano[4,3-c]isothiazole-3-carboxylate (8) in high yield. A ca. 1:1 mixture of ethyl 3-phenylisothiazole-4- and 5-carboxylates (6,7) was formed from benzonitrile sulfide and ethyl propiolate. The corresponding reaction with diethyl fumarate gave diethyl trans-4,5-dihydro-3-phenylisothiazole-4,5- dicarboylate (10). 3-Arylisothiazoles, unsubstituted at both the 4- and 5-positions, were prepared from the reaction of 5-aryl-1,3,4-oxathiazolones with norbornadiene by a pathway involving cycloaddition of the nitrile sulfide to the norbornadiene, followed by retro-Diels-Alder extrusion of cyclopentadiene from the resulting isothiazoline cycloadduct 12. In summary, the use of microwave irradiation, rather than conventional heating methods, allows nitrile sulfide generation and reactions to be carried out in shorter times, with easier work-up and, in some cases, in higher yields.

NITROGEN CONTAINING HETEROCYCLIC COMPOUNDS USEFUL AS M3-RECEPTOR MODULATORS

A compound of formula (I): Formula (I) having M3 receptor- antagonist activity or having both muscarinic receptor antagonist and ss2-agonist activity; a composition comprising such a compound; the use of such a compound in therapy (such as asthma or COPD)