Method for synthesizing lenalidomide

A technology of lenalidomide and a synthesis method, which is applied in the field of synthesizing lenalidomide, can solve the problems of low number of times of catalyst recycling, environmental pollution by harmful wastes, easy occurrence of violent explosion, etc., so as to improve the intrinsic reaction speed and improve the recovery rate. Utilization rate and the effect of increasing the number of cycles

Inactive Publication Date: 2017-08-11
HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0019] The present invention solves the problem of low yield and low purity in the traditional lenalidomide synthesis reaction, the production of a large amount of harmful waste to pollute the environment, the high cost of environmental protection treatment, the danger of violent explosion, the degradation caused by long reaction time at high temperature, and the recycling of catalysts. For the problem of low frequency, a synthetic method of lenalidomide is provided

Method used

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  • Method for synthesizing lenalidomide
  • Method for synthesizing lenalidomide
  • Method for synthesizing lenalidomide

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Experimental program
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Effect test

specific Embodiment approach 1

[0053] Take by weighing 200g of lenalidomide precursor nitro substances and add 5.0L of methanol, stir evenly, add 10g of Pd loading capacity as 10% Pd / C activated carbon catalyst, fully stir and mix to form material I; adjust the flow rate of the slurry pump to The flow rate of material I is 28.0g / min, adjust H 2 The flow rate of the gas flow meter is 300ml / min, the reaction temperature is 120°C, and the nitro group of the lenalidomide precursor and H 2 The molar ratio is 1:3.5, the residence time of the reaction is 35s, and the reaction pressure is 1.2MPa; collect the reaction liquid flowing out from the outlet of the microchannel reactor, and distill the solvent under reduced pressure at 25°C, then add 2L of DMF, and Stir for 30 minutes, then filter and recover the activated carbon catalyst with a loading capacity of 10% Pd / C, measure 6L of water and drop it into the filtrate, after about 30 minutes, a large amount of solids are precipitated, keep stirring at 0°C for 1 hour...

specific Embodiment approach 2

[0055] Take by weighing lenalidomide precursor nitro substance 200g and add 5.0L ethanol, after stirring, add 8g of Pd loading capacity as 10%Pd / C activated carbon catalyst, fully stir and mix to form material I; adjust the flow rate of slurry pump to make The flow rate of material I is 28.0g / min, adjust H 2 The flow rate of the gas flow meter is 300ml / min, the reaction temperature is 120°C, and the nitro group of the lenalidomide precursor and H 2 The molar ratio is 1:3.5, the residence time of the reaction is 35s, and the reaction pressure is 1.2MPa; collect the reaction liquid flowing out from the outlet of the microchannel reactor, and distill the solvent under reduced pressure at 25°C, then add 2L of DMF, and Stir for 30 minutes, then filter to recover the activated carbon catalyst with a loading capacity of 10% Pd / C, measure 6L of water and drop it into the filtrate, after about 30 minutes, the dropwise addition is completed, and a large amount of solid is precipitated, ...

specific Embodiment approach 3

[0057] Take by weighing 160g of lenalidomide precursor nitro substance and add 4.0L of methanol, stir evenly, add 8g of Pd loading capacity as 10% Pd / C activated carbon catalyst, fully stir and mix to form material I; adjust the flow rate of the slurry pump to The flow rate of material I is 32.0g / min, adjust H 2 The flow rate of the gas flow meter is 350ml / min, the reaction temperature is 130°C, and the nitro group of the lenalidomide precursor and H 2 The molar ratio of the reaction is 1:3.5, the residence time of the reaction is 30s, and the reaction pressure is 1.2MPa; the reaction liquid flowing out from the outlet of the microchannel reactor is collected, the solvent is recovered by distillation under reduced pressure at 25°C, and then 1.6L of DMF is added, and the Stir at low temperature for 30 minutes, then filter and recover the activated carbon catalyst with a loading capacity of 10% Pd / C, measure 4.8L of water and drop it into the filtrate, drop it in about 30 minute...

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Abstract

The invention provides a method for synthesizing lenalidomide, belongs to the field of anti-tumor and anti-leukemia medicines in organic synthesis, and particularly relates to the method for synthesizing lenalidomide. To solve the problems of low yield, low purity, environmental pollution caused by massive harmful waste, excessive cost for environment-friendly treatment, easily occurred risk of violent explosive, degradation caused by long reacting time at high temperature and low catalyst recycling frequency in a traditional lenalidomide synthesis reaction, the method comprises the following steps: 1, adding a lenalidomide precursor nitro compound into an organic solvent, adding an activated carbon catalyst having a Pd loading capacity of 10 percent, then leading the mixture serving as a material I into a pre-heating module of a microchannel reactor; and 2, respectively pumping preheated material I and a material II hydrogen into a reaction module of the microchannel reactor into a reactor, collecting outflowing reaction liquid, and treating to obtain the lenalidomide. The method is environment-friendly, and has the advantages of high reaction yield, high purity and good economical efficiency.

Description

technical field [0001] The invention belongs to the field of synthesis of antitumor and leukemia drugs in organic synthesis, and in particular relates to a method for synthesizing lenalidomide. Background technique [0002] Lenalidomide is a new immunomodulatory oral preparation developed by Gelgene in the United States for the treatment of fatal blood diseases and cancer. The molecular formula is as follows: [0003] [0004] Lenalidomide is a new-generation derivative of thalidomide. Clinical data show that its efficacy is 100 times that of thalidomide, and its efficacy has not been found to be toxic. Therefore, lenalidomide is the current It is the most effective drug for treating multiple myeloma. More than 50% of patients can significantly prolong their survival time after taking this drug. At present, there are about 300,000 people in the world suffering from myelodysplastic syndrome, and lenalidomide is currently the most effective drug that can effectively treat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCY02P20/584C07D401/04
Inventor 任吉秋杨昆
Owner HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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