Method for preparing pyridino-triazolone compound through flow chemistry

A pyridotriazolone, flow chemistry technology, applied in the chemical industry, organic chemistry, sustainable manufacturing/processing and other directions, can solve the problem of triazolone synthesis and other problems, achieve less back mixing, high mass transfer and heat transfer efficiency , the effect of high total yield

Active Publication Date: 2021-07-20
ZHEJIANG UNIV OF TECH
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention synthesizes substituted triazolone compounds under the condition of one-step oxidative rearrangement of hydrazide compounds in the p...

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
  • Method for preparing pyridino-triazolone compound through flow chemistry
  • Method for preparing pyridino-triazolone compound through flow chemistry
  • Method for preparing pyridino-triazolone compound through flow chemistry

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Add the raw material 2-phenyl-N'-(pyridin-2-yl)acetylhydrazide (30mmol) into the first storage tank, dissolve it with methanol until it is clear and set the volume to 60mL, and prepare a hydrazide concentration of 0.5mmol / mL solution, stir well before use. Add iodobenzene diacetate (33mmol) into the second storage tank, dissolve it with methanol until clarification and set volume to 66mL to prepare a solution with an oxidant concentration of 0.5mmol / mL, stir well and set aside for use.

[0027] The materials in the first storage tank and the second storage tank are conveyed by metering pumps P1 and P2 respectively (the molar flow ratio of raw materials and oxidants is 1:1.1), enter the mixer, and mix, and the mixed reaction liquid enters the tubular reaction The reactor was oxidized and rearranged, the temperature of the tubular reactor was maintained at 45°C, and the residence time of the reaction liquid in the tubular reactor was 30 minutes. The reaction ...

Embodiment 2

[0029] According to the method described in Example 1, except that acetonitrile was used instead of methanol as the solvent, the yield of the product was 31%, and the product was a white solid.

Embodiment 3

[0031] According to the method described in Example 1, except that the reaction temperature was 70° C., the yield of the product was 81%, and the product was a white solid.

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 method for preparing a pyridino- triazolone compound (II) through flow chemistry. The method comprises the following steps: a hydrazide compound (I) is dissolved in an organic solvent, the solution is placed in a first storage tank, an oxidantis dissolved in the organic solvent, and the solution is placed in a second storage tank; and aterials in the first storage tank and the second storage tank are conveyed through metering pumps respectively and enter a mixer to be mixed, reaction liquid obtained through mixing continuously enters a tubular reactor to be subjected to oxidation rearrangement reaction, the temperature of oxidation rearrangement is 0-70 DEG C, the retention time of the mixed reaction liquid in the tubular reactor is 0.1-10 h, material liquid obtained after reaction enters a receiving tank and is subjected to post-treatment, and after-treatment is conducted on the material liquid to obtain the product (II). In the tubular reaction, the material back mixing is less, the mass transfer and heat transfer efficiency is high, and the side reaction is obviously reduced; a reaction system is simple, raw materials, especially hydrazide compounds, are easily obtained, a substrate does not need to be prepared in multiple steps, and the total yield is relatively high; and the continuous tubular reaction can accurately control reaction parameters and has an automation prospect;.

Description

technical field [0001] The invention relates to a method for preparing pyridotriazolone compounds by flow chemistry. Background technique [0002] Pyridotriazolones are an important class of nitrogen-containing heterocyclic compounds in pharmacy and pesticides due to their special chemical structure and biological activity. At present, there have been many reports on active molecules containing the core of pyridotriazolone. For example, the drug trazodone is a pyridotriazolone antidepressant, and its effect is similar to that of tricyclics and monoamine oxidase inhibitors (MAOI). It is the first-line drug for clinical treatment of depression. (J. Med. Chem. 1985, 28, 1394-1398; J. Med. Chem., 1999, 42, 336-345; Bioorg. Med. Chem. Lett. 2013, 23, 3983-3987; Bioorg. Med. Chem. 2014, 22, 3414-3422; Bioorg. Med. Chem. Lett. 2015, 25 5524–5528; Bioorg. Med. Chem. Lett. 2016, 26, 3207-3211). [0003] At present, the synthesis of substituted pyridotriazolones is mainly through t...

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
IPC IPC(8): C07D471/04
CPCC07D471/04Y02P20/10
Inventor 张逢质叶增辉
Owner ZHEJIANG UNIV OF TECH
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