1835340-19-6

Basic information

• Product Name: Tedizolid Impurity 3
• Synonyms: Tedizolid Impurity 3
• CAS NO: 1835340-19-6
• Molecular Formula: C17H16FN6O6P
• Molecular Weight: 450.32
• Mol File: 1835340-19-6.mol

Chemical Properties

• Boiling Point: 725.6±70.0 °C(Predicted)
• Appearance: /
• Density: 1.75±0.1 g/cm3(Predicted)
• PKA: 1.81±0.10(Predicted)
• CAS DataBase Reference: Tedizolid Impurity 3(CAS DataBase Reference)
• NIST Chemistry Reference: Tedizolid Impurity 3(1835340-19-6)
• EPA Substance Registry System: Tedizolid Impurity 3(1835340-19-6)

Safety Data

• Hazardous Substances Data: 1835340-19-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tedizolid Impurity 3 is used as a reference material for quality control and analytical testing in the pharmaceutical industry. It helps ensure the purity, safety, and efficacy of the final drug product by providing a benchmark for comparison during the development and manufacturing process.
Used in Research and Development:
Tedizolid Impurity 3 is utilized as a research tool for studying the properties, mechanisms of action, and potential side effects of Tedizolid and ent-Tedizolid Phosphate. This information is crucial for optimizing the drug's formulation, dosage, and administration, as well as for identifying potential drug interactions and adverse effects.
Used in Regulatory Compliance:
Tedizolid Impurity 3 is employed in the regulatory process to meet the requirements of various health authorities and regulatory agencies. It serves as a reference standard for the identification, quantification, and control of impurities in the final drug product, ensuring compliance with established guidelines and standards for drug safety and quality.

Upstream product

• 856866-72-3 (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one 
• 624-28-2 2,5-dibromopyridine 
• 97483-77-7 2-Cyano-5-bromopyridine 
• 380380-64-3 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine 
• 380380-60-9 2-(1,2,3,4-tetrazol-5-yl)-5-bromopyridine 
• 372-19-0 meta-fluoroaniline 
• 72755-13-6 (3-fluoro-phenyl)-carbamic acid methyl ester 
• 149524-42-5 (5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 
• 487041-08-7 (5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one 
• 444335-16-4 (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 1188330-70-2 (R)-3-(4-bromo-3-fluoro-phenyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-oxazolidin-2-one 
• 874290-59-2 2-fluoro-4-(benzyloxycarbonyl)aminophenylboronic acid 
• 510729-01-8 (4-bromo-3-fluorophenyl)carbamic acid benzyl ester 

Relevant articles and documents

Refining process of tedizolid and preparation method of tedizolid phosphate

The invention belongs to the field of medicine synthesis, and discloses a refining process of tedizolid. According to the invention, a mixed solution of dichloromethane, toluene and ethanol is prepared, tedizolid generated through Suzuki reaction is purified through steps of liquid separation, filtration and the like, and the obtained tedizolid pure product is used for tedizolid phosphate synthesis. While the purity of tedizolid is ensured, the consumption of tedizolid in the refining process is reduced, the yield of tedizolid is improved, the utilization rate of raw materials is improved, the production cost is saved, the tedizolid with higher purity participates in synthesis of tedizolid phosphate, the side reaction in the tedizolid phosphate synthesis process is reduced, the purification difficulty of tedizolid phosphate is reduced, and the purity and the yield of tedizolid phosphate are improved. The method is suitable for refining tedizolid compounds, and is especially suitable for refining an intermediate tedizolid in a tedizolid phosphate synthesis process.

Purification method of tedizolid phosphate

The invention relates to the technical field of medicinal chemistry, in particular to a purification method of tedizolid phosphate. The method comprises the following steps: firstly, crude tedizolid phosphate is creatively mixed with absolute ethyl alcohol, impurities with lower polarity than tedizolid phosphate in the crude tedizolid phosphate are dissolved in the absolute ethyl alcohol, then the impurities are removed by filtering, and tedizolid phosphate is left in a filtered solid; and other impurities can be removed by combining the subsequent steps of converting tedizolid phosphate solid into tedizolid phosphate disodium salt, acidifying, crystallizing and the like. The tedizolid phosphate obtained through purification is high in purity, the sodium hydroxide solution is clear, and a high-boiling-point solvent which is difficult to remove does not need to be used in the purification process of the purification method. The method is simple, convenient and beneficial to industrial production.

Preparation method of tedizolid phosphate

The invention discloses a preparation method of tedizolid phosphate, and belongs to the technical field of medicines. The preparation method of tedizolid phosphate comprises the following steps: 1, synthesizing a compound IV; 2, synthesizing a compound II

Preparation method of high-purity tedizolid phosphate

The invention discloses a preparation method of high-purity tedizolid phosphate. The preparation method comprises the following steps: 1, with 2-methyl-5-(5-bromopyridin-2-yl)tetrazole as a starting material and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) as a catalyst, and reacting the starting material and the catalyst with bis(pinacolato)diboron to generate a compound as shown in a formula 1, namely bromine-converted pinacol borate; 2, subjecting a compound shown in a formula 3 and (5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one to Suzuki coupling under the catalyticaction of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) to obtain (R)-3-[4-[2-(2-methyltetrazol-5-yl)pyridin-5-yl]-3-fluorophenyl]-5-one; and 3, preparing tedizolid phosphate from a compound as shown in a formula 5 under the condition of phosphorylation of phosphorus oxychloride.

Preparation method of tedizolid phosphate and intermediate thereof

The invention discloses a preparation method of tedizolid phosphate and an intermediate thereof. The preparation method of a tedizolid phosphate intermediate II comprises the following steps: 1, in anorganic solvent, under a condition of presence of a catalyst and zinc powder, performing a reaction on 3-fluorine-4-bromophenyl amino benzyl formate so as to obtain a solution of a tedizolid phosphate intermediate III; and 2, in an organic solvent, under a condition of presence of a palladium catalyst and a base, performing a coupling reaction on the solution of the tedizolid phosphate intermediate III obtained in the step 1 with 2-methyl-5-(5-bromopyridine-2-yl) tetrazole, so as to obtain the tedizolid phosphate intermediate II. The preparation method disclosed by the invention is free of toxic reagent, mild in reaction condition, safe to operate, environmentally friendly, high in yield, high in prepared product purity and low in production cost. Tedizolid phosphate prepared from the tedizolid phosphate intermediate II disclosed by the invention is high in yield, high in purity, capable of meeting raw material medicine standards and applicable to industrial production.

Nickel catalyzed tedizolid phosphate synthesis method

The invention discloses a nickel catalyzed tedizolid phosphate synthesis method. The method includes that methyl tetrazolium bromopyridine serving as an electrophilic reagent and N-oxazolidinone phenyl zinc halide serving as a nucleophilic reagent are subjected to nickel catalyzed Negishi coupling reaction and in-situ deprotection to obtain pharmaceutically active molecular tedizolid through a two-step one-pot process, and tedizolid is subjected to phosphoric acid esterification to obtain tedizolid phosphate. The method has advantages that 1) by in-situ synthesis and utilization of the organiczinc reagent, a complex step of metal reagent separation is avoided; 2) a cheap nickel catalyzing system is applied to establishment of a tedizolid phosphate core framework for the first time, and efficiency of nickel catalyzed Negishi coupling reaction is equivalent to that of palladium catalyzed Suzuki coupling reaction in current industrial synthesis of tedizolid phosphate. The remarkable advantages are beneficial to improvement of efficiency in tedizolid phosphate synthesis and production cost reduction, and the nickel catalyzed tedizolid phosphate synthesis method has a promising industrial application prospect.

Preparation method of tedizolid phosphate

The invention belongs to the field of pharmaceutical and chemical industry, and specifically relates to a preparation method of tedizolid phosphate. The compound shown as a formula Z1 is a tedizolid phosphate precursor, and is obtained in a cyclization reaction through catalyst catalysis by using X3 as a raw material. The preparation method of the compound shown as the formula Z1 comprises the following steps: carrying out the cyclization reaction on a compound shown as a formula X2 and a compound shown as a formula R under the existence of a catalyst and a solvent, so as to obtain the compound shown as a formula Z1; carrying out a phosphorylation reaction on the compound shown as the formula Z1 so as to obtain tedizolid phosphate. According to the preparation method disclosed by the invention, the compound with high boiling point such as DMPU is prevented from being used as the catalyst, and the dissolubility of the reaction system is improved through the addition of a mixed solvent,so that the reaction time is greatly shortened, and the compound is applicable for industrial production.

Method for preparing tedizolid phosphate

The invention discloses a method for preparing tedizolid phosphate, wherein the method specifically includes the steps: with N-[3-fluoro-4-[6-(2-methyl-2H-tetrazole-5-yl)-3-pyridyl]phenyl]benzyqcarbamate as a starting raw material, in the presence of R1-O-M, 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, carrying out a reaction with R-glycidyl butyrate, and then esterfying with POCl3 phosphoric acid to obtain a tedizolid phosphate crude product; and adjusting the pH value to 7-9 with an alkali solution, converting the tedizolid phosphate crude product into a salt, and adjusting the pH value to 1-2 with hydrochloric acid to obtain the refined tedizolid phosphate. The method has the advantages of mild reaction conditions, relatively low cost, simple and convenient operation, less side reaction, high yield, good reaction reproducibility, economy and environmental protection, and is suitable for industrialized production.

A high-purity extreme zuozuo amine phosphorus ester preparation method

The invention discloses a preparation method for high-purity tedizolid phosphate. The method is characterized by comprising the following steps: subjecting starting materials tedizolid and phosphorus oxychloride to a reaction so as to produce a tedizolid phosphorus oxychloride intermediate; then reacting the tedizolid phosphorus oxychloride intermediate with benzyl alcohol so as to produce a tedizolid dibenzyl phosphate intermediate; and carrying out debenzylation under the action of a catalyst so as to obtain tedizolid phosphate. Meanwhile, all the parameters of procedures are systematically adjusted. The introduced dibenzyl phosphate intermediate has good stability; benzyl protection removal reaction conditions are mild; compared with conventional preparation methods for tedizolid, by-reactions and generation of impurities are greatly reduced in the invention; the purity of the prepared tedizolid phosphate can reach more than 99.9%; and the preparation method omits the step of product purification, has more simplified steps and improves preparation efficiency of the tedizolid phosphate.

A process for the preparation of key intermediate thiazolylamine specially phosphate and its preparation method (by machine translation)

The invention discloses a key intermediate for preparing tedizolid phosphate. The key intermediate has a structure shown in formula I: R is any one of R1 or R2, and the R1 and R2 are independently selected from aryl groups or replaced aryl groups. The invention further discloses a preparation method of the key intermediate, and a method for preparing tedizolid phosphate by the key intermediate. The key intermediate disclosed by the invention is a solid compound and is easy to purify; besides, dipolymers, multimers and hydrolysis impurities cannot be generated during the preparation of tedizolid phosphat, the reaction temperature is moderate, the operation is simple, a strong-acidity reagent (phosphorus oxychloride) is prevented from being used, and the preparation method belongs to an environment-friendly production technology.