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Method for preparing ML264 key intermediate

A technology for ML264 and intermediates, applied in the direction of organic chemistry, etc., can solve the problems of difficult preparation and extraction of key intermediates of ML264, low yield, high extraction cost, etc., and achieve the effect of simple reaction operation, easy-to-obtain materials and low cost

Inactive Publication Date: 2015-01-07
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of method for preparing ML264 key intermediate to prepare and extract ML264 key intermediate relatively difficult for existing various methods, such as low yield, high extraction cost, greatly improve yield, reduce cost of production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A method for preparing ML264 key intermediates, comprising the following steps:

[0022] 1) Add 740 mg of tetrahydrothiopyran-4-one 1,1-dioxide and 5.30 g of sodium triacetoxyborohydride into a 100 mL flask, add a stirring magnet, 30 mL of acetonitrile, and methanol solution of methylamine at room temperature ( 30%) 12mL, put the reaction bottle in a stirrer, add 0.58mL glacial acetic acid after stirring for 4min, and stir for 48h; point the TLC plate during the reaction process to determine the degree of reaction, and the light yellow liquid that can be obtained after the end of the reaction is confirmed;

[0023] 2) At room temperature, add 20mL of water and 60mL of dichloromethane / methanol (10:1) solution in batches to the light yellow liquid in step 1), and extract multiple times (5 times);

[0024] 3) The organic phase obtained after step 2) was spin-dried to obtain the crude product ML264 key intermediate;

[0025] 4) The crude product was separated by column chr...

Embodiment 2

[0027] 1) Add 1,480 mg of tetrahydrothiopyran-4-one 1,1-dioxide and 10.60 g of sodium triacetoxyborohydride into a 100 mL flask, add a stirring magnet, 60 mL of acetonitrile, and methanol solution of methylamine at room temperature ( 30%) 24mL, put the reaction bottle in a stirrer, add 1.2mL glacial acetic acid after stirring for 4min, and stir for 48h; point the TLC plate during the reaction process to determine the degree of reaction, and the light yellow liquid that can be obtained after the reaction is confirmed;

[0028] 2) At room temperature, add 60mL saturated sodium bicarbonate solution and 180mL dichloromethane / methanol (10:1) solution in batches to the light yellow liquid in step 1), and extract multiple times (4 times);

[0029] 3) The organic phase obtained after step 2) was spin-dried to obtain the crude product ML264 key intermediate;

[0030] 4) The crude product was separated by column chromatography with a mixture of dichloromethane / methanol (10:1) and a smal...

Embodiment 3

[0032] A method for preparing ML264 key intermediates, comprising the following steps:

[0033] 1) Add 370 mg of tetrahydrothiopyran-4-one 1,1-dioxide and 2.10 g of sodium triacetoxyborohydride into a 100 mL flask, add a stirring magnet, 30 mL of acetonitrile, and a methanol solution of methylamine at room temperature ( 30%) 6mL, put the reaction bottle in a stirrer, add 0.29mL glacial acetic acid after stirring for 4min, and stir for another 48h; point the TLC plate during the reaction process to determine the reaction degree, and the light yellow liquid that can be obtained after the reaction is confirmed;

[0034] 2) At room temperature, add 20mL sodium bicarbonate solution and 60mL dichloromethane / methanol solution (10 / 1, volume ratio) in batches to the light yellow liquid in step 1), and extract multiple times (6 times);

[0035] 3) The organic phase obtained after step 2) was spin-dried to obtain the crude product ML264 key intermediate;

[0036] 4) The crude product wa...

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PUM

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Abstract

The invention provides a method for preparing an ML264 key intermediate. Tetrahydrothiapyranyl-4-one-1,1-dioxide used as an initial raw material is subjected to one-step reaction to synthesize the ML264 key intermediate. The reagents used by the method are laboratory common reagents, and the key step reduction reaction in the reaction can be performed at room temperature, so that the method has the advantages of accessible materials and low cost, is simple to operate and easy to treat, and can obtain abundant ML264 key intermediate for medicine research and development.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a method for preparing a key intermediate of ML264. Background technique [0002] KLF5, also known as BTEB2 and IKLF, belongs to the KLF family. As a basic transcription factor, it regulates many important target genes, such as cyclin B, cyclinD1, FGF-BP and PDGFA. KLF5 has an integral role in cell cycle regulation, apoptosis, differentiation and migration. A large number of research results have fully confirmed that KLF5 is highly expressed in a variety of tumor cells and promotes tumor proliferation, and is a potential therapeutic target. Therefore, inhibiting KLF5 in cells and animals will effectively inhibit the proliferation of these tumor cells, and small molecules that inhibit KLF5 may be developed into new anti-tumor drugs. [0003] Vincent W. Yang's research group adopted the ultra-high-throughput screening (μHTS) strategy, and at the same time used the s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/02
CPCC07D335/02
Inventor 陈海军郑小梅王旋旋胡子旋高瑜
Owner FUZHOU UNIV