One-pot synthesis method of anticancer drug ceritinib intermediate 1-(isopropylsulfonyl)-2-nitrobenzene

A technology of propylsulfonyl and ceritinib, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as high energy consumption and long reaction time, and achieve low energy consumption and reduced production The effect of high cost and purity

Inactive Publication Date: 2015-05-06
常州百敖威生物科技有限公司
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This technology involves reacting two chemical compounds together without adding any other substances like water or alcohol that could smell bad on their own skin when they were extracted from them by means such as evaporation techniques. By replacing certain components instead of just water or an alkali metal salt called ammonia into these reactions, it becomes easier to produce highly pure products due to less heat required compared to traditional methods. Additionally, this process can lead to higher yields than previous processes but lower costs because fewer steps needed.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding new ways to make certain types of drugs more effective against specific diseases such as brain tumours like glioblastoma multiforme and histeous carcinomas called advanced adenocarccytsis type IIa.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • One-pot synthesis method of anticancer drug ceritinib intermediate 1-(isopropylsulfonyl)-2-nitrobenzene
  • One-pot synthesis method of anticancer drug ceritinib intermediate 1-(isopropylsulfonyl)-2-nitrobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add DMF (423.3g), 60% sodium hydride (44g, 1.1moL) and o-fluoronitrobenzene (141.1g, 1.0moL) to a reaction flask equipped with a liquid caustic tail gas absorption device, and control the temperature with an ice-water bath at 0 ℃, add isopropyl mercaptan (91.4g, 1.2moL) dropwise, the dropwise addition is completed, rise to 25℃ and react for 2.0-3.0h, the central control o-fluoronitrobenzene disappears, the reaction is completed, control the temperature at 25℃, and add dropwise Acetic acid (72.6g, 1.2moL), 30% hydrogen peroxide (340.1g, 3.0moL), after the dropwise addition, slowly raise the temperature to 80-100°C for 3.0-4.0h until 2-(isopropylsulfide)nitrobenzene disappear. Cool to 25°C, pour the reaction solution into ice water (2L), extract with dichloromethane (300mL*3), wash the organic layer with saturated sodium bicarbonate solution (300mL*3), water (300mL) successively, and dry In the organic layer, dichloromethane was distilled off under reduced pressure to ob...

Embodiment 2

[0031] Add DMF (564.4g), 60% sodium hydride (48g, 1.2moL) and o-fluoronitrobenzene (141.1g, 1.0moL) to a reaction flask equipped with a liquid caustic tail gas absorption device, and control the temperature with an ice-water bath at 0 ℃, add isopropyl mercaptan (99g, 1.3moL) dropwise, the dropwise addition is completed, rise to 25℃ and react for 2.0-3.0h, the central control o-fluoronitrobenzene disappears, the reaction is completed, control the temperature at 25℃, and then add acetic acid dropwise (78g, 1.3moL), 30% hydrogen peroxide (340.1g, 3.0moL), after the dropwise addition, slowly raise the temperature to 80-100°C for 3.0-4.0h until 2-(isopropylsulfide)nitrobenzene disappears. Cool to 25°C, pour the reaction solution into ice water (3L), extract with dichloromethane (300mL*3), wash the organic layer with saturated sodium bicarbonate solution (300mL*3), water (300mL), and dry In the organic layer, dichloromethane was distilled off under reduced pressure to obtain 189.5 g...

Embodiment 3

[0033] Add DMF (564.4g), 60% sodium hydride (60g, 1.5moL) and o-fluoronitrobenzene (141.1g, 1.0moL) to a reaction flask equipped with a liquid caustic tail gas absorption device, and control the temperature with an ice-water bath at 0 ℃, add isopropyl mercaptan (114.2g, 1.5moL) dropwise, the dropwise addition is completed, rise to 25℃ and react for 2.0-3.0h, the central control o-fluoronitrobenzene disappears, the reaction is completed, control the temperature at 25℃, and add dropwise Acetic acid (90g, 1.5moL), 30% hydrogen peroxide (453.4g, 4.0moL), after the dropwise addition is completed, slowly raise the temperature to 80-100°C for 3.0-4.0h until 2-(isopropylsulfide)nitrobenzene disappears . Cool to 25°C, pour the reaction solution into ice water (3L), extract with dichloromethane (300mL*3), wash the organic layer with saturated sodium bicarbonate solution (300mL*3), water (300mL), and dry In the organic layer, dichloromethane was distilled off under reduced pressure to o...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a one-pot synthesis method of an anticancer drug ceritinib intermediate 1-(isopropylsulfonyl)-2-nitrobenzene, which comprises the following steps: adding ortho-fluoronitrobenzene and sodium hydride into a solvent DMF (N,N-dimethylformamide), adding isopropyl mercaptan, reacting completely to obtain a 2-(isopropylthioether)nitrobenzene reaction solution, dropwisely adding acetic acid into the 2-(isopropylthioether)nitrobenzene reaction solution, carrying out oxydol oxidizing reaction, and after the reaction is complete, carrying out after-treatment to obtain the 1-(isopropylsulfonyl)-2-nitrobenzene. The potassium carbonate is changed into the strong alkali sodium hydride, thereby greatly lowering the reaction temperature and enhancing the reaction rate; after the synthetic reaction of the 2-(isopropylthioether)nitrobenzene, the next oxidizing step is directly performed without after-treatment, thereby avoiding the stink caused by after-treatment; and the method is applicable to industrial production, is convenient to operate, and is economical and environment-friendly.

Description

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Owner 常州百敖威生物科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap