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Preparation method of apatinib

A technology of apatinib and compounds, applied in the field of preparation of apatinib, can solve problems such as increased cost, harsh conditions, and increased difficulty

Active Publication Date: 2018-08-17
YANCHENG TEACHERS UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of raw material preparation, the method needs to control the temperature at -10~0°C, the conditions are relatively harsh, which increases the difficulty of the reaction, and the raw material II table is more expensive, which increases the cost of the reaction

Method used

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  • Preparation method of apatinib
  • Preparation method of apatinib
  • Preparation method of apatinib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Embodiment 1: the preparation of 2-(4-aminophenyl) acetonitrile (compound 2)

[0092] Compound 1 (10g, 61.67mmol) was dissolved in methanol (50ml), added 10% Pd / C (1.0g), and washed with H 2 Replacement reaction system four times, in H 2 Stir overnight at room temperature under ambient (0.5 MPa). TLC analysis showed that the reaction was complete. The reaction liquid was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure to obtain 8.08 g of compound 2 with a yield of 99.1%.

Embodiment 2

[0093] Embodiment 2: the preparation of 2-(4-aminophenyl) acetonitrile (compound 2)

[0094] Compound 1 (10g, 61.67mmol) was dissolved in methanol (50ml), added 5% Pd / C (1.2g), and washed with H 2 Replacement reaction system four times, in H 2 Stir overnight at room temperature under ambient (1 MPa). TLC analysis showed that the reaction was complete. The reaction liquid was filtered through celite, and the filtrate was concentrated under reduced pressure to obtain 7.99 g of compound 2 with a yield of 98.1%.

Embodiment 3

[0095] Example 3: Preparation of N-(4-(aminomethyl)phenyl)-2-nitronicotinamide (compound 4)

[0096] Compound 3 (16.8 g, 0.1 mol) was dissolved in acetonitrile (100 ml), carbonyldiimidazole (19.46 g, 0.12 mol) was added, and stirred at room temperature for 2 hours. Compound 2 (17.18 g, 0.13 mol) was added, the temperature was raised to 85° C., and the temperature was kept for 6 hours. After the reaction, the acetonitrile was distilled off to obtain an oil, and pure water (80ml) was added thereto, stirred with a glass rod to precipitate a solid, filtered, rinsed with water, and dried to obtain 22.92g of compound 4 with a yield of 81.2%.

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Abstract

The invention discloses a preparation method of apatinib and belongs to the field of medicine and fine chemical industry. The preparation method is a novel preparation scheme; a target compound that is satisfactory can be acquired with any intermediate. The preparation method has the advantages the advantages of short procedure, simple reacting steps, good safety and reliability, high yield, low cost, high purity, low pollution, good operational simplicity and the like.

Description

technical field [0001] The invention relates to a preparation method of apatinib, which belongs to the fields of medicine and fine chemical industry. Background technique [0002] Apatinib (Apatinib), the molecular formula is C 24 h 23 N 5 O, whose chemical name is N-[4-(1-cyanocyclopentyl)phenyl]-2-(4-pyridylmethyl)amino-3-pyridinecarboxamide, is a new type of tyrosine kinase inhibitor . The specific structure of Apatinib is as follows: [0003] [0004] As a new generation of tyrosine kinase inhibitors, apatinib has been clinically proven to be effective, safe and well tolerated in the treatment of patients with advanced gastric cancer. The drug is the first to demonstrate the efficacy of anti-angiogenic small molecule targeted drugs in gastric cancer. Tyrosine kinase vascular endothelial growth factor (VEGF) and its receptor (VEGFR) play an extremely important role in tumor angiogenesis, and are important targets in blocking tumor angiogenesis. Vascular endothel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82A61K31/444A61P35/00C07C253/30C07C255/42
CPCA61K31/444A61P35/00C07C253/30C07C255/42C07D213/82
Inventor 张立洁孙雅泉顾惠雯
Owner YANCHENG TEACHERS UNIV
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