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Refining method of triazine compounds

A refining method and compound technology, applied in organic chemistry and other directions, can solve the problems of high impurity III content and low product purity, and achieve the effects of high product purity, controllable single impurity content, and short cycle time.

Inactive Publication Date: 2018-10-16
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The invention provides a method for refining compound I, the purpose of which is to solve the problem of low product purity and high content of main impurity III

Method used

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  • Refining method of triazine compounds
  • Refining method of triazine compounds
  • Refining method of triazine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 5g of compound I with a content of 98.6% into a 500ml three-necked flask, then add 60g of ethanol, 55g of water, 15g of sodium hydroxide, and 0.25g of activated carbon in sequence, start stirring, and heat to a slight reflux state. The system temperature is 78-79°C. Continue to reflux and stir for 2 hours, filter while it is hot, keep the system temperature not lower than 55°C during filtration, stir and cool the filtrate to crystallize to 3°C, keep stirring for 10 hours, then filter, wash the filter cake with 95% ethanol, vacuum the filter cake After drying, the temperature of the vacuum drying oven was set at 42° C., and the drying time was 10 hours. 4.6 g of white crystals of Compound I were obtained, with a content of 99.61%, impurity III content of 0.03%, and other impurities less than 0.1%.

Embodiment 2

[0023] Add 5g of compound I with a content of 98.6% in a 500ml three-necked flask, then add 50g of ethanol, 50g of water, 17g of sodium hydroxide, and 0.3g of activated carbon in sequence, start stirring, and heat to a slight reflux state. The system temperature is 78-79°C. Continue to reflux and stir for 2.5 hours, filter while it is hot, keep the system temperature not lower than 55°C during filtration, stir and cool the filtrate to crystallize to 2°C, keep stirring for 11 hours, then filter, wash the filter cake with 95% ethanol, vacuum the filter cake After drying, the temperature of the vacuum drying oven was set at 42° C., and the drying time was 10 hours. 4.4 g of white crystals of compound I were obtained, with a content of 99.64%, impurity III content of 0.04%, and other impurities less than 0.1%.

Embodiment 3

[0025] Add 5g of compound I with a content of 98.6% into a 500ml three-necked flask, then add 60g of ethanol, 60g of water, 15g of sodium hydroxide, and 0.3g of activated carbon in sequence, start stirring, and heat to a slight reflux state. The system temperature is 78-79°C. Continue to reflux and stir for 3 hours, filter while it is hot, keep the system temperature not lower than 55°C when filtering, stir and cool the filtrate to crystallize to 2°C, keep stirring for 12 hours, then filter, wash the filter cake with 95% ethanol, vacuum the filter cake After drying, the temperature of the vacuum drying oven was set at 42°C, and the drying time was 10 hours. 4.7 g of white crystals of compound I were obtained, with a content of 99.65%, impurity III content of 0.02%, and other impurities less than 0.1%.

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Abstract

The invention discloses a refining method of triazine compounds in a formula I. The refining method includes steps: adding a crude product of a compound I into a mixed solvent of ethyl alcohol, water,sodium hydroxide and activated carbon, heating to 78-79 DEG C to achieve a micro reflux state, continuing reflux stirring for 2-4h, filtering as soon as possible, subjecting filtrate to stirring andcooling to 0-5 DEG C to realize crystallization, keeping the temperature for 10-12h, filtering, and performing vacuum drying to obtain a pure product of the compound I, wherein the pure product is higher than 99.5% in purity, lower than 0.1% in single impurity content and lower than 0.5% in total impurity content and meets requirements of general medicine content.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a method for refining triazine compounds. Background technique [0002] Chinese patent CN105175410A has reported the following formula I with structure [0003] [0004] The preparation method and activity test of the compound, the activity test shows that the compound I has a good anti-tumor proliferation effect. However, according to the preparation method of the last step, as shown in the figure below, [0005] [0006] This step reaction mainly exists the impurity compound III shown in the following formula, [0007] [0008] Its structure was confirmed by H NMR and mass spectrometry: 1H NMR (400MHz, DMSO-d6): δppm 7.98(d,1H), 7.62(s,1H),7.41(d,1H),3.74-3.70(m,8H ),3.03-2.97(m,4H),2.66-2.51(m,6H),2.37(m,2H),2.09(s,1H),1.52(m,2H),1.36(t,3H); ESI / MS: m / z=536 (M+H)+. According to the post-processing method reported in the patent, the purity of the obtained produ...

Claims

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Application Information

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IPC IPC(8): C07D417/14
CPCC07D417/14
Inventor 许慧邓泽平成佳陈芳军
Owner 湖南华腾制药有限公司