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The preparation method of ponatinib

A technology of ponatinib and compounds, applied in the field of preparation of ponatinib, can solve the problems of high cost and unsatisfactory target product yield, and achieve the effects of wide temperature range, reduced synthesis cost and easy control of conditions

Active Publication Date: 2020-04-17
深圳蓝新科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to overcome the above-mentioned deficiency of prior art, provide a kind of preparation method of ponatinib, use expensive catalyst to solve the synthetic method of existing ponatinib, cost is high, the yield of target product is not ideal technical problem

Method used

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  • The preparation method of ponatinib
  • The preparation method of ponatinib
  • The preparation method of ponatinib

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preparation example Construction

[0016] The invention provides a preparation method of ponatinib. The preparation method of described ponatinib comprises the steps:

[0017] S01. Compounds A, B, and E of the following structural formula are provided, wherein the R contained in the compound A 1 is H, a halogen atom, and the R contained in the compound E 2 is a halogen atom:

[0018]

[0019] S02. In a protective atmosphere, the compound A and the compound B are subjected to light reaction in an organic solvent containing an acridinium salt photocatalyst, a copper salt, and an alkalinity to generate a compound C of the following structural formula;

[0020] S03. reacting the compound C with tetrabutylammonium fluoride to generate the compound D of the following structural formula;

[0021] S04. In a protective atmosphere, the compound D and the compound E are subjected to photoreaction in an organic solvent containing an acridinium salt photocatalyst, a copper salt, and an alkalinity to generate ponatinib...

Embodiment 2

[0050] This embodiment provides a preparation method of ponatinib. The preparation method of described ponatinib is as follows:

[0051] (1) Compound A and Compound B are added to an acetonitrile solvent containing CuCl and diisopropylamine, and illuminated by a blue LED light source for 24 hours to generate the target product Compound C; wherein, Compound A1mmol, Compound B1.2mmol, CuCl is 0.01 mmol, 0.05 mmol of acridinium salt, 2 equivalents of diisopropylamine, and 2 mL of acetonitrile solvent.

[0052] (2) Purifying Compound C and reacting it with tetrabutylammonium fluoride in tetrahydrofuran to generate the target product Compound D;

[0053] (3) Compound D and Compound E are added to an acetonitrile solvent containing CuCl and diisopropylamine, and illuminated by a blue LED light source for 10 hours to generate the target product ponatinib; wherein, Compound D1mmol, Compound E 1.1mmol, CuCl The concentration of the acridine salt is 0.03mmol, the acridinium salt is 0....

Embodiment 3

[0059] This embodiment provides a preparation method of ponatinib. The preparation method of described ponatinib is as follows:

[0060] (1) Compound A and Compound B are added to a DMF solvent containing CuBr and diisopropylamine, and illuminated by a blue LED light source for 48h to generate the target product Compound C; wherein, Compound A1mmol, Compound B1.2mmol, CuCl 0.05mmol , 0.05 mmol of acridinium salt, 2 equivalents of diisopropylamine, and 1.5 mL of DMF solvent.

[0061] (2) Purifying Compound C and reacting it with tetrabutylammonium fluoride in tetrahydrofuran to generate the target product Compound D;

[0062] (3) Compound D and Compound E are added to the DMF solvent containing CuBr and diisopropylamine, and illuminated by a blue LED light source for 10 hours to generate the target product ponatinib; wherein, compound D1mmol, compound E 1.1mmol, CuCl The concentration of DMF is 0.03mmol, that of acridinium salt is 0.03mmol, that of diisopropylamine is 1.2mmol...

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Abstract

The invention discloses a preparing method of ponatinib. The preparing method of ponatinib comprises the steps of building a reaction system in copper salt and alkaline organic solvent with 3-halogen-parazole [1,5-a]pyrimidine being the starting point, with trimethylsilylacetylene, tetrabutylammonium fluoride and the like being raw materials in sequence and with acridine salt being a photocatalyst, and thus indirectly building a synthesizing path of ponatinib. The synthesis conditions are mild, the cost is low, and the yield of ponatinib is high.

Description

technical field [0001] The invention belongs to the technical field of organic medicinal chemistry, and in particular relates to a preparation method of ponatinib. Background technique [0002] Ponatinib is an anticancer drug. In December 2012, it was approved by the US FDA for the treatment of adult chronic myelogenous leukemia (CML) and "Philadelphia chromosome positive" (Ph+) acute lymphoblastic leukemia (ALL). [0003] According to literature reports, the current synthetic method of ponatinib is mainly obtained according to the following synthetic route and conditions: [0004] [0005] But above-mentioned synthesis method needs to use expensive palladium catalyst, must need heating, and productive rate is low. This will be one of the main reasons affecting the high price of this kind of drug raw material, thereby causing a heavy burden on patients. Contents of the invention [0006] The object of the present invention is to overcome the above-mentioned deficienc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 黄湧张健叶韩珂珩周海鹏王雷锋丁小妹韩辉张强
Owner 深圳蓝新科技有限公司
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