182760-06-1

Usage

Uses

Used in Pharmaceutical Industry:
4-[2-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile is used as a pharmaceutical compound for its potential therapeutic applications. The compound's unique structure may allow it to interact with specific biological targets, making it a candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, 4-[2-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)b utan-2-yl]-1,3-thiazol-4-yl]benzonitrile can be used as a starting material or a building block for the synthesis of more complex molecules with various applications, such as agrochemicals, dyes, or advanced materials.
Used in Material Science:
The compound's specific structural features may also make it suitable for use in material science, where it could be employed in the development of new materials with unique properties, such as improved conductivity or enhanced stability.

InChI:InChI=1/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-7-6-17(23)8-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1

Upstream product

• 20099-89-2 4-Cyanophenacyl bromide 
• 170863-34-0 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 86404-63-9 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone 
• 219872-85-2 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanamide 
• 166948-49-8 (2R,3R)-3-[3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-3-(1H-1,2,4-triazol-1-yl)]butanoic acid 
• 861718-83-4 (S)-3-chloro-2-(2,4-difluorophenyl)-2-((trimethylsilyl)oxy)propanenitrile 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 124627-86-7 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 
• 132507-89-2 (2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 1175536-51-2 (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide hydrosulfate 
• 170862-36-9 (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile 
• 861718-85-6 3-chloro-2-(2,4-difluorophenyl)-2-(trimethylsilanyloxy)propionaldehyde 

Downstream Products

• 351227-63-9 di-tert-butyl-[{(1R,2R)-2-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-1-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-ylmethyl)propyl}-oxy]methyl phosphate 
• 251295-70-2 carbonic acid chloromethyl ester 2-[4-(4-cyanophenyl)-thiazol-2-yl]-1-(2,4-difluorophenyl)-1-[1,2,4]triazol-1-yl-methylpropyl ester 
• 251295-69-9 (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-[[[m-chloromethyl]benzoyloxy]methoxy]butane 
• 1022985-55-2 4-(2-((R)-1-((R)-6-(2,4-difluorophenyl)-8-oxo-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-6-yl)ethyl)thiazol-4-yl)benzonitrile 
• 1022985-62-1 2-[3-[4-(4cyanophenyl)-thiazol-2-yl]-2-(2,4-difluorophenyl)-2-hydroxy-butyl]-2H-[1,2,4]triazole-3-carboxylic acid chloromethyl ester 
• 207224-83-7 (2R,3R)-2-(2,4-Difluoro-phenyl)-1-[1,2,4]triazol-1-yl-3-{4-[4-(1H-[1,2,4]triazol-3-yl)-phenyl]-thiazol-2-yl}-butan-2-ol 
• 368421-60-7 4-{2-[(1R,2R)-2-(2,4-Difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-thiazol-4-yl}-thiobenzamide 

Relevant academic research and scientific papers

AN IMPROVED PROCESS FOR THE PREPARATION OF TRIAZOLE DERIVATIVES

The present invention relates to an improved process for the preparation of triazole derivatives such as ravuconazole and isavuconazole.

An enantioselective synthesis of the key intermediate for triazole antifungal agents; Application to the catalytic asymmetric synthesis of efinaconazole (jublia)

A new synthetic route, the shortest reported to date, to access a key intermediate for the synthesis of various triazole antifungal agents was developed. The elusive tetrasubstituted stereogenic center that is essential in advanced triazole antifungal agents was constructed via the catalytic asymmetric cyanosilylation of a ketone. The subsequent transformations were performed in two one-pot operations, enhancing the overall synthetic efficiency toward the intermediate. This streamlined synthetic approach was successfully applied to efficient enantioselective syntheses of efinaconazole (Jublia) and ravuconazole.

Process for the manufacture of enantiomerically pure antifungal azoles as ravuconazole and isavuconazole

A new technical process for preparation of enantiomerically pure antifungal compounds of formula I by resolution of the racemates has been disclosed.

Improved chiral synthesis of ravuconazole

A short, elegant, and high yielding synthesis of ravoconazole is presented. The key step of this synthesis is an enantioselective palladium-catalyzed chiral zinc-allene addition reaction. The starting materials are 2-chloro-1-(2,4-difluorophenyl)-ethanone and (R)-4-phenylbutyn-2-ol obtained from enzymatic resolution of its racemate. Copyright Taylor & Francis Group, LLC.

The process development of ravuconazole: An efficient multikilogram scale preparation of an antifungal agent

The development of a safe, robust process for the preparation of ravuconazole (1), an antifungal agent, is described. The discovery and development of procedures enabling the efficient synthesis of multikilogram quantities of 1 and the process demonstration through plant scale preparations are presented. A controlled means to prepare a Grignard reagent and utilization of Fourier Transform Infrared spectroscopy (FTIR) monitoring to safely conduct the reaction is featured.

Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives

A series of novel thiazole-containing triazole antifungals was synthesized and evaluated for antifungal activity against a variety of clinically isolated pathogenic fungi in vitro and against systemic candidosis in vivo. These compounds showed potent antifungal activities in vitro and in vivo. In particular, (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4- difluorophenyl)-1-(1H-1,2,4-triazol-l-yl)-2-butanol (12g; ER-30346) showed potent and well-balanced in vitro activities and potent in vivo efficacy, and had a good safety profile.