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Preparation method of chlorinated linezolid impurity

A technology of linezolid and chlorination, which is applied in the field of medicine, can solve the problems of inability to obtain pure impurities and low conversion rate, and achieve the effect of reducing the risk of use, high conversion rate and mild conditions

Pending Publication Date: 2021-12-21
SUZHOU SIXTH PHARMA PLANT OF JIANGSU WUZHONG PHARMA GROUP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Therefore, the technical problem to be solved in the present invention is to overcome the defect that the conversion rate is low and cannot obtain pure impurities in the synthesis process of linezolid chlorinated impurities in the prior art, thereby providing a new linezolid chlorinated impurity preparation method

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  • Preparation method of chlorinated linezolid impurity
  • Preparation method of chlorinated linezolid impurity
  • Preparation method of chlorinated linezolid impurity

Examples

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Embodiment 1

[0048] This embodiment provides a linezolid chlorinated impurity represented by formula V, and its reaction equation and preparation method are as follows:

[0049]

[0050] (1) Take 3.0g of the compound of formula I, 2.0g of potassium phthalimide, and 30ml of DMF and heat together for 5 hours at a temperature of 115±5°C. After the reaction is completed, add water to precipitate the product, filter and dry, 3.5 g of N-(3-phthalimido-2-hydroxypropyl)-3-chloro-4-morpholinoaniline (compound of formula II) was obtained;

[0051] (2) Preparation of N-[3-[(3-chloro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl]-phthalimide: Mix 3.5 g of the compound of formula II obtained in the previous step, 2.0 g of carbonyldiimidazole (CDI), and 40 g of dichloromethane, react at room temperature for 20 hours, wash with water after the reaction, dry over anhydrous sodium sulfate, and evaporate to dryness under reduced pressure. Then recrystallize with ethanol to get N-[3-[(3-chloro-4-morpho...

Embodiment 2

[0059] This embodiment provides a linezolid chlorinated impurity represented by formula V, and its reaction equation and preparation method are as follows:

[0060]

[0061] (1) Heat 32.1g of the compound of formula I, 20.0g of potassium phthalimide, and 320ml of DMF at a temperature of 115±5°C for 5 hours. After the reaction, add water to precipitate the product, filter and dry, Obtained 32.8g, and recrystallized with isopropanol to obtain 16.1g of N-(3-phthalimido-2-hydroxypropyl)-3-chloro-4-morpholinoaniline (compound of formula II);

[0062] (2) 16.0 g of the compound of formula II obtained in the previous step, 8.0 g of triphosgene, 10.0 g of triethylamine, and 100 ml of dichloromethane were mixed, reacted at room temperature for 20 hours, washed with water after the reaction, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure . Then recrystallize with ethanol to get N-[3-[(3-chloro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]-p...

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Abstract

The invention provides a preparation method of a chlorinatedlinezolid impurity. The preparation method specifically comprises the following steps: (1) reacting a compound shown as a formula I with potassium phthalimide to obtain a compound shown as a formula II; (2) carrying out amidation reaction on the compound shown in the formula II to obtain a compound shown in a formula III; (3) performing deprotection on the compound in the formula III to obtain a compound in a formula IV; and (4) carrying out acetylation reaction on the compound in the formula IV to obtain a compound in a formula V. According to the method, the compound in the formula I is innovatively taken as a raw material to react with potassium phthalimide, then acylation cyclization is carried out, and then deprotection and acetylation reaction are carried out, so that the route is reasonable, the condition is mild, and the product purity is high.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method of linezolid chlorinated impurities. Background technique [0002] Linezolid is a synthetic oxazolidinone antibacterial drug developed by Pfizer Inc. in the United States. It was approved by the FDA in April 2000 for the treatment of infections caused by Gram-positive (G+) cocci, including those caused by Suspected or confirmed hospital-acquired pneumonia (HAP), community-acquired pneumonia (CAP), complicated skin or skin and soft tissue infection (SSTI) and vancomycin-resistant enterococcus (VRE) infection caused by MRSA. It was subsequently launched in many countries. Entered China in 2007, the trade name is Swan. [0003] The dosage forms of linezolid include injections, tablets, and dry suspensions, among which injections account for more than 80% of sales. [0004] The earliest marketed injection was Linezolid Glucose Injection, and later Pfizer developed Line...

Claims

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Application Information

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IPC IPC(8): C07D263/20
CPCC07D263/20
Inventor 陈燕武卫邓银来高怡蓉钱轩徐兰兰
Owner SUZHOU SIXTH PHARMA PLANT OF JIANGSU WUZHONG PHARMA GROUP
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