166196-11-8

Usage

Uses

Used in Pharmaceutical Industry:
1-[(2,6-Difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxylic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with improved efficacy and selectivity, making it a valuable asset in drug discovery and design.
Used in Chemical Synthesis:
In the field of chemical synthesis, 1-[(2,6-Difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxylic acid serves as a versatile building block for the creation of a wide range of chemical products. Its reactivity and structural diversity enable the synthesis of complex molecules with specific properties, such as novel materials, agrochemicals, and specialty chemicals.
Used in Material Science:
1-[(2,6-Difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxylic acid can be utilized in the development of advanced materials with unique properties. Its incorporation into polymers, for example, can lead to materials with enhanced thermal stability, mechanical strength, and chemical resistance, making them suitable for various applications in the automotive, aerospace, and electronics industries.
Used in Research and Development:
As a novel chemical entity, 1-[(2,6-Difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxylic acid holds significant potential for research and development purposes. It can be employed as a model compound to study various chemical reactions and mechanisms, as well as to explore new synthetic routes and methodologies in organic chemistry.

Upstream product

• 217448-86-7 methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate 
• 869501-51-9 1-(2,6-difluorobenzyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester 
• 106308-60-5 2-(azidomethyl)-1,3-difluorobenzene 
• 471-25-0 Propiolic acid 
• 1364193-40-7 [1-(2,6-difluorobenzyl)-1H-1,2,3-triazol-4-yl]methanol 
• 85118-00-9 2,6-Difluorobenzyl bromide 
• 697-73-4 2,6-difluorobenzyl chloride 

Downstream Products

• 217448-86-7 methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate 
• 106308-44-5 rufinamide 

Relevant academic research and scientific papers

Highly regioselective and sustainable solar click reaction: A new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide-alkyne cycloaddition reaction

The synthesis of pharmaceutically active 1,2,3-triazoles has been continuously scrutinized in the search for unique and effective catalysts to make the process efficient, green, and sustainable. Here, we are presenting a new visible light active Ni(ii) cyclam-integrated triazole-linked organic polymer (Ni-TLOP) photocatalyst for the synthesis of 1,2,3-triazole compounds with excellent efficiency and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic system sustainable and environmentally friendly. This photocatalyzed click reaction technique has been successfully applied to the expedient synthesis of one of the most sold anti-epileptic drugs rufinamide.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

SUBSTITUTED TRIAZOLES AND METHODS RELATING THERETO

Substituted 1,2,3-triazole compounds are disclosed which have utility in the treatment of a variety of neurological disorders. The compounds provided herein have the general structure wherein R1, R2, R3 and n are as defined herein, including stereoisomers, esters, solvates and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound provided herein in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for treating neurological disorders in a subject in need thereof.

PROCESS FOR PREPARATION OF RUFINAMIDE

The present invention relates to a novel process for preparation of rufinamide (I) comprising: reacting 2,6-difluorobenzyl azide (II) and propiolic acid (III) in a mixture of alcohol and water to produce 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (IV), esterifying the acid (IV) to ester (V) and treating ester (V) with ammonia. The invention further relates to process for purification of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (IV), by crystallization from a mixture of alcohol and water. The present invention also provides process for purification of rufinamide (I) by crystallization from mixture of polar aprotic solvent with water or alcohol.

PROCESS FOR PREPARATION OF RUFINAMIDE

The invention relates to a novel, industrially viable, cost effective process for the preparation of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide commonly known as Rufinamide and intermediates thereof.

PROCESS FOR PREPARATION OF RUFINAMIDE

The present invention relates to a novel process for preparation of rufinamide (I) comprising: reacting 2,6-difluorobenzyl azide (II) and propiolic acid (III) in a mixture of alcohol and water to produce 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxyl

IMPROVED PROCESS FOR THE PREPARATION OF RUFINAMIDE

The invention relates to a novel, industrially viable, cost effective process for the preparation of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide commonly known as Rufinamide and intermediates thereof.

PROCESS FOR PREPARATION OF FLUORINATED TRIAZOLE COMPOUND

The present invention discloses a process for the preparation of 1-[(2,6-difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide of Formula (I), comprising regioselective cycloaddition of 2,6-difluorobenzyl halide of Formula (II), wherein X is chloride, br

IMPROVED PROCESS FOR PREPARING RUFINAMIDE INTERMEDIATE

The present invention refers to an improved method for the preparation of compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid substantially free of its 3H-I isomer. The invention also refers to the use of said intermediate for the preparation of Rufinamide and for obtaining a new polymorphic form of Rufinamide, designed as Form R-5. The invention also refers to said new polymorph of Rufinamide, and to the composition containing it and its use as medicament. The new polymorph of Rufinamide shows good stability and appropriate physico-chemical properties for its manipulation on industrial scale. Polymorph Form R-5 will be suitable to use as pharmaceutical for the treatment of convulsions, especially for the treatment of epilepsy.

METHOD FOR THE PREPARATION OF RUFINAMIDE

The invention provides a novel process for the regioselective preparation of a compound of formula (I)