135270-13-2

Basic information

• Product Name: 135270-13-2
• Synonyms: 1-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole;Efinaconazole Related Impurity 6;1-[[(2R,3R)-2-(2,4-Difluorophenyl)-3-methyl-2-oxiranyl]methyl]-1H-1,2,4-triazole
• CAS NO: 135270-13-2
• Molecular Formula: C₁₂H₁₁F₂N₃O
• Molecular Weight: 251.2320464
• EINECS: -0
• Mol File: 135270-13-2.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 371.6±52.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• PKA: 2.75±0.10(Predicted)
• CAS DataBase Reference: 135270-13-2(CAS DataBase Reference)
• NIST Chemistry Reference: 135270-13-2(135270-13-2)
• EPA Substance Registry System: 135270-13-2(135270-13-2)

Safety Data

• Hazardous Substances Data: 135270-13-2(Hazardous Substances Data)

Usage

Description

135270-13-2, also known as (2R,3R)-2-(2,4-Difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane, is a synthetic intermediate with significant applications in the pharmaceutical industry. It is characterized by its unique chemical structure, which includes a 2,4-difluorophenyl group, a methyl group, and a 1,2,4-triazole ring, all of which contribute to its versatile reactivity and potential uses.

Uses

Used in Pharmaceutical Industry:
135270-13-2 is used as a synthetic intermediate for the production of (2R,3S)-Efinaconazole (E435080), a potent topical antifungal agent specifically designed for the treatment of onychomycosis. Its unique chemical structure allows for the efficient synthesis of the desired enantiomer, which exhibits high efficacy against fungal infections.
The application of 135270-13-2 in the pharmaceutical industry is primarily due to its role in the synthesis of Efinaconazole, a drug that has shown promising results in treating onychomycosis, a common fungal infection that affects the nails. By serving as a key intermediate in the synthesis process, 135270-13-2 plays a crucial role in the development and production of this important antifungal medication.

Upstream product

• 132507-89-2 (2R,3S)-2-(2,4-Difluoro-phenyl)-1-[1,2,4]triazol-1-yl-butane-2,3-diol 
• 124-63-0 methanesulfonyl chloride 
• 126918-20-5 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,2,3-butanetriol 
• 132563-81-6 1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one 
• 126918-19-2 (2S,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-butane-1,2-diol 
• 126918-18-1 (2S^*,3R^*)-2-(2,4-Difluorophenyl)-1-(dimethylisopropoxysilyl)-3-(tetrahydropyran-2-yloxy)-2-butanol 
• 126918-21-6 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol 
• 132507-77-8 Trifluoro-acetic acid (1R,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 124627-86-7 (2R^*,3S^*)-2-(2,4-Difluorophenyl)-3-methyl-2-<(1H-1,2,4-triazol-1-yl)methyl>oxirane 
• 132507-89-2 threo-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 126945-34-4 Methanesulfonic acid (1S,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 41253-21-8 sodium triazole 
• 1829-92-1 triethylsulfonium iodide 
• 86404-63-9 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone 

Downstream Products

• 132507-77-8 Trifluoro-acetic acid (1R,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 

Relevant articles and documents

NOVEL METHOD FOR PREPARATION OF EPOXYTRIAZOLE DERIVATIVES

The present invention relates to novel processes for preparing epoxytriazole derivatives. The method of claim 1, further comprising the step of adding a base to the intermediate compound. The present invention relates to an epoxytriazole derivative and a manufacturing method thereof. Chemical Formula 1. Here, Ar denotes C. 6 -C10 Aryl group or C aryl group2 -C9 The aryl group 1 -4 is substituted or unsubstituted, and when 2 or more halogen is substituted, the heteroaryl group may be the same as or different from each other, and the heteroaryl group is represented by 1 -4 fluorine, chlorine, or C. 1 -C3 Substituted or unsubstituted alkyl groups, and fluorine, chlorine, or C. 1 -C3 When more than 2 substituents are substituted, each of these substituents may be the same or different and may be different from each other. The A is C. 1 -C3 Represents an alkyl group, and the R represents an alkyl group. 1 And R2 Is a methyl group or an ethyl group.

METHOD FOR PREPARATION OF EFINACONAZOLE IN IONIC LIQUID MEDIUM

The present invention relates to a novel method for preparation of efinaconazole in an ionic liquid medium, the method comprising: reacting 1-[[(2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole, and 4-methylenepiperidine or an organic chemically acceptable salt thereof, wherein the 4-methylenepiperidine or the organic chemically acceptable salt thereof is anionized on a base; and performing a coupling reaction with the 1-[[(2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole in the presence of an ionic liquid compound. The present invention uses an ionic liquid instead of an organic solvent when preparing efinaconazole, thereby reducing related substances compared to the conventional method, shortens the reaction time, thereby making it possible to easily obtain the final compound, efinaconazole, with high purity and high yield, and may be very suitably used for mass production.

PROCESS FOR PRODUCING EPOXY ALCOHOL COMPOUND

A compound represented by formula (II): (where Ar represents a phenyl group optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom and a trifluoromethyl group, and R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms) is produced by step A: reacting trimethyl oxosulfonium salt or trimethyl sulfonium salt with a base in a solvent, and removing the resulting solid to obtain a trimethyl oxosulfonium ylide solution or a trimethyl sulfonium ylide solution; and step B: reacting a compound represented by formula (I): and the solution obtained in step A, and the compound represented by formula (II) can be derived to a compound represented by formula (V): that is useful for production of an antifungal agent.