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Method for separating and purifying substituted indazole isomers

A technology for separation and purification of isomers, applied to the separation and purification of 1-position and 2-position substituted indazole isomers, and the field of separation and purification of substituted indazole isomers, which can solve the problems of poor selectivity and unsuitability for industrial production, etc. problem, to achieve the effect of simple operation, practical method and few steps

Inactive Publication Date: 2012-05-09
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the current preparation process of indazole derivatives substituted by 1-position and 2-position, due to the poor selectivity of the 1-position and 2-position functionalization reactions, resulting in the generation of mixtures, the current separation and purification methods are column chromatography, which is not suitable for in industrial production

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  • Method for separating and purifying substituted indazole isomers
  • Method for separating and purifying substituted indazole isomers

Examples

Experimental program
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Effect test

Embodiment 1

[0016] The separation and purification method of 5-amino-1-(2-hydroxyethyl)-indazole and 5-amino-2-(2-hydroxyethyl)-indazole mixture is as follows: mix 10g of the above mixture with 30mL acetone / Mix 10mL of water, heat to dissolve, then naturally cool and filter to obtain 5.3g of 5-amino-1-(2-hydroxyethyl)-indazole with a purity of 99.5%. The characteristics are as follows:

[0017] 1 H NMR (DMSO-d6): δ2.05 (d, J = 18.9Hz, 2H), 4.16 ~ 4.18 (m, 2H), 4.54 ~ 4.56 (m, 2H), 7.54 (d, J = 7.2Hz, 1H ), 8.25(s, 1H), 8.29(dd, J=1.5, 1.5Hz, 1H), 8.74(d, J=1.5Hz, 1H). MS(ESI) m / z 178(M+H) + .

[0018] Obtain 3.6 g of 5-amino-2-(2-hydroxyethyl)-indazole with a purity of 99.6%, and its characteristics are as follows:

[0019] 1 H NMR (DMSO-d6): δ4.17~4.19(m, 2H), 4.61~4.63(m, 2H), 7.76(d, J=7.2Hz, 1H), 8.13(dd, J=1.5, 1.5Hz , 1H), 8.30(s, 1H), 8.74(d, J=1.2Hz, 1H). MS(ESI) m / z 178(M+H) + .

Embodiment 2

[0021] The separation and purification method of 5-amino-1-(2-hydroxyethyl)-indazole and 5-amino-2-(2-hydroxyethyl)-indazole mixture is as follows: mix 10g of the above mixture with 20mL acetone / 40mL of water was mixed, heated to dissolve, then naturally cooled and filtered to obtain 3.2g of 5-amino-2-(2-hydroxyethyl)-indazole with a purity of 99.8%; 5-amino-1-(2-hydroxyethyl) - Indazole 4.8 g, purity 99.5%. Its characteristics are as in Example 1.

Embodiment 3

[0023] The separation and purification method of 5-amino-1-(2-hydroxyethyl)-indazole and 5-amino-2-(2-hydroxyethyl)-indazole mixture is as follows: mix 8g of the above mixture with 16mL ethanol / 30mL of water was mixed, heated to dissolve, then naturally cooled and filtered to obtain light red needle-like crystals, 4.7g of 5-amino-1-(2-hydroxyethyl)-indazole, with a purity of 99.2%; 5-amino-2- (2-Hydroxyethyl)-indazole 4.3 g, purity 99.3%.

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Abstract

The invention discloses a method for separating and purifying substituted indazole derivative isomers with structural general formulas shown in the specification, which belongs to the field of organic chemistry. In the method, a mixed solvent is used for recrystallizing; and two indazole derivative isomers are separated to obtain a single isomer compound with the purity of over 99 percent. The method has the advantages of simple and convenient separation and purification and easy industrialized production.

Description

technical field [0001] The invention relates to a separation and purification method of substituted indazole isomers, in particular to a separation and purification method of 1-position and 2-position substituted indazole isomers, belonging to the field of organic chemistry. Background technique [0002] Indazole compounds are important drug intermediates, and their derivatives have the functions of NO synthase inhibition, sperm production inhibition, pain relief, anti-virus, and HIV protease inhibition, so they have good effects in anti-tumor, virus and fungal treatments. Application prospects, the research on the synthesis and biological activity of indazole derivatives has received extensive attention in recent years. Since the indazole nucleus is very rare in nature, its artificial synthesis is very important. The 1-position and 2-position of indazole are active amine groups, which can easily introduce a variety of active groups, and the derivatives are all biologically...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/56
Inventor 石伟民陶京朝张运晓张根
Owner ZHENGZHOU UNIV