164650-45-7

Basic information

• Product Name: S,S-Efinaconazole
• Synonyms: (alphaS,betaS)-alpha-(2,4-Difluorophenyl)-beta-methyl-4-methylene-alpha-(1H-1,2,4-triazol-1-ylmethyl)-1-piperidineethanol;Efinaconazole Related Impurity 3;(2S,3S)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;ent-Efinaconazole;S,S-Efinaconazole
• CAS NO: 164650-45-7
• Molecular Formula: C18H22F2N4O
• Molecular Weight: 348.3902864
• EINECS: -0
• Mol File: 164650-45-7.mol

Chemical Properties

• Boiling Point: 512.2±60.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• PKA: 12.11±0.29(Predicted)
• CAS DataBase Reference: S,S-Efinaconazole(CAS DataBase Reference)
• NIST Chemistry Reference: S,S-Efinaconazole(164650-45-7)
• EPA Substance Registry System: S,S-Efinaconazole(164650-45-7)

Safety Data

• Hazardous Substances Data: 164650-45-7(Hazardous Substances Data)

Usage

Uses

ent-Efinaconazole is the S,S-enantiomer of Efinaconazole (E435070); a topical antifungal for onychomycosis.

Upstream product

• 148133-82-8 4-methylene piperidine 
• 135270-07-4 (2S,3R)-2-(2,4-difluorophenyl)-3-methyl-2-<(1H-1,2,4-triazol-1-yl)methyl>oxirane 
• 124627-86-7 1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)-methyl)-1H-1,2,4-triazole 
• 144230-50-2 4-methylenepiperidine monohydrochloride 
• 144230-50-2 4-methylenepiperidine hydrochloride 
• 861718-83-4 (S)-3-chloro-2-(2,4-difluorophenyl)-2-((trimethylsilyl)oxy)propanenitrile 
• 861718-85-6 3-chloro-2-(2,4-difluorophenyl)-2-(trimethylsilanyloxy)propionaldehyde 
• 127000-91-3 (2R,3R)-3-Amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 86404-63-9 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone 
• 102429-07-2 2-bromo-2',4'-difluoroacetophenone 
• 372-18-9 1,3-Difluorobenzene 
• 164650-61-7 para-toluenesulphonic acid efinaconazole salt 

Relevant articles and documents

Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents

An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.

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.

PREPARATION METHOD FOR EFINACONAZOLE

The present invention provides a preparation method for Efinaconazole, comprising the following steps: in the presence of a bromide and a base, subjecting (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazole-1-yl)methyl]oxirane and an inorganic a

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 THE PREPARATION OF AN AZOLIC DERIVATIVE

The present invention refers to a process for the preparation of an azolic derivative used in the treatment of onychomycosis. Said process comprises the reaction between (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane and 4-methylenepiperidine or a salt thereof, in the presence of a zinc derivative in an alcoholic solvent.

Anti-Selective Catalytic Asymmetric Nitroaldol Reaction of α-Keto Esters: Intriguing Solvent Effect, Flow Reaction, and Synthesis of Active Pharmaceutical Ingredients

A rare-earth metal/alkali metal bimetallic catalyst proved particularly effective for enantioselectively coupling nitroalkanes and α-keto esters in an anti-selective manner to afford synthetically versatile, densely functionalized, and optically active α-nitro tertiary alcohols. A chiral diamide ligand captured two distinct metal cations, giving rise to a catalytically competent solid-phase heterobimetallic catalyst by simple mixing via self-assembly. The advantage of the solid-phase asymmetric catalyst was realized by successful application to the enantio- and diastereoselective reaction in a continuous-flow platform. The use of closely related solvents in terms of structures and polarity parameters, THF and its methylated congener 2-Me-THF, had an unexpectedly large solvent effect both on the reaction rate and the stereoselectivity. The nitroaldol products share a privileged unit for active pharmaceutical ingredients, as demonstrated by the streamlined enantioselective synthesis of the marketed antifungal agents efinaconazole and albaconazole.

Preparing method of 1-triazole-2-butanol derivative

The invention relates to a preparing method of a 1-triazole-2-butanol derivative. The preparing method comprises the steps of making 4-methylpiperidine addition salt react with (2R,3S)-2-(2,4-di-fluorophenyl)-3-methyl-2-[(1H-1,2,4-traizole-1-radical)methy

METHOD OF PRODUCING 1-TRIAZOLE-2-BUTANOL DERIVATIVES

PROBLEM TO BE SOLVED: To provide a novel method of producing 1-triazole-2-butanol derivatives useful as pharmaceuticals. SOLUTION: A method of producing a 1-triazole 2-butanol derivative represented by formula (1) comprises reacting a compound represented by formula (2) with 4-methylenepiperidine (3) in the presence of a metal salt (excluding lithium salts). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

A Facile Epoxide Aminolysis Promoted by (t-BuO)2Mg and Its Application to the Synthesis of Efinaconazole

A novel and efficient method for the aminolysis of trizole epoxides is described. This method consists of a facile ring opening of the epoxides mediated by t-BuOMgCl generated in situ from amine hydrochlorides and (t-BuO)2Mg. The desired β-amino alcohols were obtained in good yields without employing other heavy metals or precious catalysts. The optimized conditions were successfully applied to the synthesis of a number of potential triazole antifungal compounds as well as efinaconazole on up to a 700 g scale.