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Tedizolid impurity and preparing method thereof

A technology of tedizolid and impurities, which is applied in the field of drug synthesis, can solve the problems of uncontrolled impurities, no public reports of impurities, etc., and achieve the effect of quality assurance, fewer steps, and simple operation methods

Inactive Publication Date: 2017-04-19
REYOUNG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current patent only controls the impurities in the synthesis process of tedizolid phosphate, and does not control the impurities in the synthesis process of tedizolid
[0006] The tedizolid process impurity is of great significance to the in-depth study of tedizolid, but there is no public report of the impurity in the prior art. The structural formula of the impurity is as follows:

Method used

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  • Tedizolid impurity and preparing method thereof
  • Tedizolid impurity and preparing method thereof
  • Tedizolid impurity and preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Nitrogen protection, add 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine (10g, 41.6mmol), (6-(2-methyl-2H-tetrazole -5-yl)pyridin-3-yl)boronic acid (8.5g, 41.6mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (304mg, 0.416mmol), potassium carbonate (11.5g, 83.2mmol) and 20mL of a mixture of tetrahydrofuran and water (1:1, V / V), heated to 30 ° C, stirred for 4 hours, TLC detected that the reaction was complete, added 20ml of water, filtered to obtain tedizolid impurity I 12.6g.

Embodiment 2

[0032] Nitrogen protection, add 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine (21g, 62.4mmol), (6-(2-methyl-2H-tetrazole -5-yl)pyridin-3-yl)boronic acid pinanol ester (11.9g, 41.6mmol), bis(triphenylphosphine)palladium dichloride (292mg, 0.416mmol), sodium tert-butoxide (6.2g, 83.2mmol) and 30mL toluene, the temperature was raised to 110° C., and the reaction was stirred for 5 hours. TLC detected that the reaction was complete, and filtered to obtain 11.9 g of tedizolid impurity I.

Embodiment 3

[0034] Under nitrogen protection, add 5-iodo-2-(2-methyl-2H-tetrazol-5-yl)pyridine (11.9g, 41.6mmol), (6-(2-methyl-2H-tetra Azol-5-yl)pyridin-3-yl)boronic acid (4.25g, 20.8mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (304mg, 0.416mmol), tert Sodium butoxide (8.0 g, 83.2 mmol) and 20 mL of dioxane were heated up to 80° C., stirred and reacted for 2 hours. TLC detected that the reaction was complete, and filtered to obtain 12 g of tedizolid impurity I.

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Abstract

The invention relates to a tedizolid impurity and a preparing method thereof, and belongs to the technical field of drug synthesis. The tedizolid impurity exists in the following tedizolid steps, and please see the steps in the specification, wherein X is fluorine, chlorine, bromine, iodine, tosylate or methanesulfonate, and R is organic boronic acid organic borate ester; and please see the structural formula of the impurity in the specification. The tedizolid impurity is of great significance in deep surveying of the tedizolid. The invention further provides a preparing method which is simple in process.

Description

technical field [0001] The invention relates to a tedizolid impurity and a preparation method thereof, belonging to the technical field of medicine synthesis. Background technique [0002] Tedizolid is an oxazolidinone antibiotic developed by Cubist Pharmaceuticals. Tedizolid was approved by the US FDA in June 2014 to be marketed in the US under the trade name Sivextro. The drug is the first second-generation oxazolidinone antibiotic approved by the FDA. Compared with the first-generation product linezolid, Sivextro has 2-8 times higher inhibitory activity against some bacteria in vitro, and its safety is also to a certain extent. improved. Since the compound Tedizolid does not yet have a standard Chinese translation, the applicant hereby transliterates it as "tedizolid". [0003] The preparation method of tedizolid has been reported and studied, patents CN200480037612 and CN200980140144 both report the synthesis method of tedizolid. [0004] [0005] Patent CN2010800...

Claims

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Application Information

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IPC IPC(8): C07D401/14
CPCC07D401/14
Inventor 苗得足胡清文赵磊于志波王宏光
Owner REYOUNG PHARMA
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