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Synthetic method of imatinib

A kind of synthetic method, the technology of imatinib

Active Publication Date: 2015-04-22
BEIJING MEDIKING BIOPHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention adopts the method of synthesizing imatinib with multiple components in one step, which solves the problem of many steps in the traditional method, and the advantage of the method is that the route is short and the efficiency is high

Method used

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  • Synthetic method of imatinib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Under nitrogen protection, 10 mmol of 4-(3-pyridyl)-2-aminopyrimidine (CAS: 66521-66-2), 10 mmol of 4-chloromethylbenzoyl (3-bromo-4-methyl phenyl)amine (CAS: 1072105-05-5), 10 mmol of N-methylpiperazine (CAS: 109-01-3), 0.2 mmol of cuprous iodide, 0.2 mmol of N,N'- Diisopropylethylenediamine and 110 mmol of sodium acetate were dissolved in 20 mL of 1,4-dioxane, and the temperature of the reaction system was 100° C. for 4 hours to react.

[0022] After the reaction, the solvent was evaporated to dryness with a rotary evaporator, and the residue was separated by column chromatography to obtain 4.2 g of imatinib with a yield of 86%.

[0023] This reaction formula is as follows:

[0024]

Embodiment 2

[0026] Other conditions are the same as in Example 1, and the reactions of using different copper salts and their dosages are tested, and the experimental results are shown in Table 1.

[0027] Table 1 Test of different catalysts and their dosage effects

[0028] serial number Copper salt (amount mol / %) Yield(%) 1 Copper acetate (2) 56 2 Copper Bromide (2) 67 3 Copper Chloride (2) 70 4 Copper Sulfate (2) 55 5 Cuprous bromide (2) 78 6 Cuprous iodide (2) 86 (Example 1) 7 Cuprous iodide (1) 80 8 Cuprous iodide (3) 84 9 Cuprous iodide (4) 78 10 Cuprous iodide (5) 73

[0029] As can be seen from the above results, the use of 2 mol% cuprous iodide is the best, as in Example 1.

Embodiment 3

[0031] Other conditions are the same as in Example 1, and the reactions under different alkalis and different dosages thereof are checked, and the experimental results are as shown in Table 2.

[0032] Table 2 Test of different alkalis and their dosage effects

[0033] serial number Alkali (amount mol / %) Yield(%) 1 Sodium acetate (110) 86 (Example 1) 2 Sodium Carbonate (110) 64 3 Sodium Citrate (110) 60 4 Sodium acetate (100) 84 5 Sodium acetate (120) 80

[0034] From the above results, it can be seen that the effect of using 110 mol% sodium acetate is the best (Example 1).

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Abstract

The invention discloses a synthetic method of imatinib, which relates to the technical field of production processes of western medicines. The method is implemented by taking copper salt and alkali as catalysts and taking N,N'-diisopropylethylenediamine as a ligand through the step of under the protection of nitrogen, in an ether solvent, carrying out hybrid reaction on 4-(3-pyridyl)-2-aminopyrimidine, 4-chloromethyl benzoyl (3-bromo-4-methylphenyl) amine and N-methyl piperazine, so that imatinib is obtained. The invention is a method for synthesizing imatinib in one step by using multiple components, which is short in route and high in efficiency.

Description

technical field [0001] The invention relates to the technical field of production technology of western medicine, in particular to a synthesis method of imatinib. Background technique [0002] Imatinib is an oral drug for the treatment of adult patients with Philadelphia chromosome (Bcr-Abl) positive chronic myelogenous leukemia (CML) in blast phase, accelerated phase and chronic phase after failure of interferon therapy . [0003] At present, there are many synthetic methods of imatinib, but most of them adopt multi-step synthetic methods. Its main fragments, pyrimidine part, amide part and N-methylpiperazine, are synthesized in multiple steps one by one, which has many steps and high cost, and also causes serious pollution to the environment, which is not conducive to mass production and sales cost. Contents of the invention [0004] The purpose of the present invention is to provide a simple, low-cost, environmentally friendly synthesis method for imatinib. [0005] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 俞磊张凯陈丰林韩哲
Owner BEIJING MEDIKING BIOPHARM