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Preparation method of alkynyl-containing compound and intermediate thereof

A compound and alkyl technology, which is applied in the field of preparation of alkyne-containing compounds and their intermediates, can solve the problems of restricting large-scale production, and achieve the effects of novel design routes, convenient utilization and operation, and mild reaction conditions

Active Publication Date: 2022-03-11
ASCENTAGE PHARMA SUZHOU CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, known methods limit large-scale production

Method used

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  • Preparation method of alkynyl-containing compound and intermediate thereof
  • Preparation method of alkynyl-containing compound and intermediate thereof
  • Preparation method of alkynyl-containing compound and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0264] step 1:

[0265]

[0266] Under the protection of nitrogen, N-methylpyrrolidone (137.6g) was heated to 30-35°C to obtain compound of formula 1 (14.4g, 1.3eq), compound of formula 2 (19.14g, 1eq), and dichloride bis Palladium (triphenylphosphate) (0.46g, 0.01eq) and cuprous iodide (0.113g, 0.01eq) were then added triethylamine (9.45g, 1.5eq) under nitrogen. The reaction mixture was heated to 65 to 75°C and maintained at this temperature for 2 hours. The process control of the reaction is carried out by liquid phase detection. When the content of the compound of formula 2 is ≤0.1%, the reaction is terminated. After the reaction, the reaction solution was cooled to 35-45°C, and N-acetyl-L-cysteine ​​(1g, 0.1eq) was added directly. The reaction was carried out with stirring for 4 to 5 hours. The resulting product was cooled to room temperature, precipitated by adding water, centrifuged, and washed with pure water to obtain a coarse filter cake. After the coarse filt...

Embodiment 2

[0278] Carry out Sonogashira reaction (other parameters are with the first step of embodiment 1) with reference to each row reaction parameter of table 4, calculate yield by formula 2 compound and be shown in the last column of table 4.

[0279] Table 4

[0280]

[0281]

Embodiment 3

[0283] The amidation reaction is carried out with reference to the reaction parameters of each row in Table 5 (other parameters are the same as the third step in Example 1), and the calculated yield of the compound of formula 4 or 5 in moles is shown in the last column of Table 5.

[0284] table 5

[0285]

[0286]

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PUM

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Abstract

The invention provides a method for preparing alkynyl-containing compounds as shown in the following formula (I) and intermediates and related compounds of the alkynyl-containing compounds. Also provided are pharmaceutical compositions comprising the compounds and methods of treating cancer thereof.

Description

technical field [0001] Provided herein are methods of making compounds containing an alkynyl moiety and methods of their use in the treatment of cancer. Certain compounds related to the methods are also provided. Background technique [0002] Cancer has a major impact on societies worldwide. Cancer is the second most common cause of human death after cardiovascular disease. The National Cancer Institute estimates that in 2015, approximately 1,658,370 new cases of cancer will be diagnosed in the United States and 589,430 people will die from the disease. [0003] Chronic myelogenous leukemia (CML) is a cancer of certain blood-forming cells that begins in the bone marrow. CML cells contain an abnormal gene, BCR-ABL, that causes CML cells to grow and multiply uncontrollably. BCR-ABL is a type of protein called a tyrosine kinase. Tyrosine kinase inhibitors (TKIs) targeting BCR-ABL are the standard treatment for CML. [0004] Imatinib It is the first drug that specificall...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D213/61C07D295/135C07C233/36C07C211/52C07C69/76A61P35/00A61K31/496
CPCC07D471/04C07D213/61C07D295/135C07C233/36C07C211/52C07C69/76A61P35/00A61K45/06C07D519/00C07C233/40
Inventor 温剑锋冯建鹏吴天助蔡民民滕尚军
Owner ASCENTAGE PHARMA SUZHOU CO LTD
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