241479-72-1

Basic information

• Product Name: 2,3-Butanediol, 2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-, (2R,3R)- (2R,3R)-2-(2,5-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol
• Synonyms: 2,3-Butanediol, 2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-, (2R,3R)- (2R,3R)-2-(2,5-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol;(2R,3R)-2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butane-2,3-diol;(2R,3R)-2-(2,5-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol;(2R,3R)-2-(2,5-difluoro-phenyl)-1-(1H-1,2,4-triazole-1-yl)butan-2,3-diol
• CAS NO: 241479-72-1
• Molecular Formula: C₁₂H₁₃F₂N₃O₂
• Molecular Weight: 269.2473264
• EINECS: -0
• Mol File: 241479-72-1.mol

Chemical Properties

• Boiling Point: 485.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• PKA: 11.94±0.29(Predicted)
• CAS DataBase Reference: 2,3-Butanediol, 2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-, (2R,3R)- (2R,3R)-2-(2,5-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Butanediol, 2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-, (2R,3R)- (2R,3R)-2-(2,5-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol(241479-72-1)
• EPA Substance Registry System: 2,3-Butanediol, 2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-, (2R,3R)- (2R,3R)-2-(2,5-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol(241479-72-1)

Safety Data

• Hazardous Substances Data: 241479-72-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Butanediol, 2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-, (2R,3R)(2R,3R)-2-(2,5-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol is used as an intermediate in the synthesis of various pharmaceutical compounds due to its unique structural features. The presence of the triazole ring and the difluorophenyl group may contribute to the development of new drugs with specific biological activities.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,3-Butanediol, 2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-, (2R,3R)(2R,3R)-2-(2,5-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol can be utilized as a building block for the creation of more complex molecules with potential applications in various industries, such as materials science, agrochemicals, and specialty chemicals.
Used in Antifungal Agents:
As an impurity in Efinaconazole, a topical antifungal used for onychomycosis, 2,3-Butanediol, 2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-, (2R,3R)(2R,3R)-2-(2,5-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol may have implications for the efficacy and safety of the drug. Further research may be necessary to understand its role in the overall pharmacological profile of Efinaconazole.

Upstream product

• 241479-69-6 (2R)-2',5'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone 
• 899819-34-2 (2,5-difluorophenyl)magnesium bromide 
• 399-94-0 2-bromo-1,4-difluorobenzene 
• 288-88-0 1,2,4-Triazole 
• 832152-04-2 (2R,3R)-3-(2,5-difluorophenyl)-3,4-epoxy-2-butanol 
• 367-30-6 2,5-difluoroaniline 

Downstream Products

• 241479-73-2 (2R,3S)-2-(2,5-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)-methyl]-oxirane 
• 241479-74-3 (2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile 
• 241479-67-4 Isavuconazole 

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.

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.

Synthetic method for antifungal drug intermediate (2R,3S)-1-(1,2,4-triazol)-2-difluorophenyl-2,3-epoxybutane

The invention discloses a synthetic method for an antifungal drug intermediate (2R,3S)-1-(1,2,4-triazol)-2-difluorophenyl-2,3-epoxybutane. The synthetic method comprises the following steps: (1) reacting a compound IV with a Grignard reagent to obtain a compound III; (2) employing a one-pot reaction to react the compound III with trimethylsulfoxonium iodide and 1,2,4-triazole and then react with p-toluenesulfonic acid, so as to obtain a compound II; and (3) reacting the compound II with methanesulfonyl chloride under an alkali condition to generate the target compound I, wherein the Grignard reagent is 2,4-difluorophenylmagnesium bromide or 2,5-difluorophenylmagnesium bromide, and the structural formula of the compound IV is shown in the specification. According to the synthetic route, the reaction conditions are mild and easy to control, the reaction route is simple, the related solvents in the reaction process all are common solvents, the reaction conversion rate is high, and the method possesses extremely high feasibility, is beneficial for industrialized batch production, and possesses extremely large exploitation potential and extremely good application prospect.

NOVEL STABLE POLYMORPHS OF ISAVUCONAZOLE OR ITS SALT THEREOF

The present invention relates to novel stable novel stable polymorphs of Isavuconazole or its salt thereof, having purity more than 90 % when measured by HPLC. In particular the present invention directs process for the preparation of solid amorphous and crystalline form of Isavuconazole base. In a further embodiment present invention directs to crystalline form Isavuconazole Hydrobromide salt and oxalate salt of 2-(2,5-difluoro- phenyl)-1-[1,2,4]triazol-1-yl-butane-2,3-diol.

A PROCESS FOR THE PREPARATION OF ISAVUCONAZOLE AND ITS INTERMEDIATES

The present invention relates to a process for the preparation of Isavuconazole or its pharmaceutical acceptable salt thereof. In particular aspects of the present invention relates to a process for the preparation of intermediate of azole intermediate. In a further aspect, the present invention relates to a process for the preparation of triazole intermediate. In a further aspect, the present invention relates to a process for the preparation of oxirane intermediate.

Azoles for treatment of fungal infections

Azole derivatives of the formula I wherein R14, R15are each independently hydrogen or fluorine, T is a group of the formula: wherein R9is pyrrolidinyl or a group A—NH—B—, A is hydrogen or straight-chain or branched C1-C5alkyl; B is straight-chain or branched C1-C4alkylene, —CH2—CONH—CH2or —CH2CH2CH2—CH(NH2); and X?is a pharmaceutically acceptable anion; and pharmaceutically acceptable salts of said compounds, and hydrates and solvates of the compounds of formula I and the salts thereof can be used in the production of medicaments for treating fungal infections and mycoses.