Method for preparing compound

A compound and drug technology, applied in the field of chemistry, can solve problems such as intractable, toxic, and need for further development and research, and achieve the effect of equipment and environment friendliness

Inactive Publication Date: 2017-12-08
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many reports on the synthesis of quinazolinones containing substituents, but most of them use metal-catalyzed methods, which usually require toxic or refractory oxidants
[0003] Furthermore, the process for preparing 6,7-disubstituted quinazolinones remains to be further developed and studied

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0023] 2-Amino-4,5-bis[(2-methoxy)-ethoxy]-benzamide (cas:236750-62-2, 2.84g, 10mmol) and paraformaldehyde (600mg, 20mmol mono Body) [monomer molar ratio: 1:2] was added to the reaction flask, then 10ml of water was added, sealed and heated to 130 degrees, reacted for 24 hours, then stood still, filtered out the solid, and recrystallized it with ethyl acetate , 2.70 g of 6,7-bis[(2-methoxy)-ethoxy]-quinazolinone can be obtained with a yield of 92%. The synthetic reaction formula is as follows:

[0024]

Embodiment 2

[0026] 2-Amino-4-methoxy-5-[(3-morpholinyl)-propoxy-]-benzamide (cas: 246512-44-7, 3.09 g, 10 mmol) was mixed with paraformaldehyde ( 600mg, 20mmol monomer) [monomer molar ratio: 1:2] was added to the reaction flask, then 10ml of water was added, sealed and heated to 130 degrees, reacted for 48 hours, then stood still, filtered out the solid, and washed it with acetic acid Ethyl ester was recrystallized to obtain 2.80 g of 7-methoxy-6-[(3-morpholinyl)-propoxy-]-quinazolinone with a yield of 88%. The synthetic reaction formula is as follows:

[0027]

Embodiment 3

[0029] 2-Amino-4,5-bis[(2-methoxy)-ethoxy]-benzamide (cas:236750-62-2, 2.84g, 10mmol) and paraformaldehyde (7.50g, 250mmol monomer) [monomer molar ratio: 1:25] was added to the reaction flask, then 10ml of water was added, sealed and heated to 130 degrees, reacted for 12 hours, then stood still, filtered out the solid, and weighed it with ethyl acetate Crystallize to obtain 2.64 g of 6,7-bis[(2-methoxy)-ethoxy]-quinazolinone with a yield of 90%. The synthetic reaction formula is as follows:

[0030]

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Abstract

The invention provides a method for preparing a compound as shown in a formula I which is described in the specification. The method comprises a step of contacting a compound as shown in a formula III which is described in the specification or a derivative thereof with a compound as shown in a formula II which is described in the specification so as to obtain the compound as shown in the formula I. In the formulas, R1 and R2 are hydrogen, alkoxy groups or heteroaromatic rings, preferably alkoxy groups; and R is hydrogen, an alkyl group, a phenyl group, a substituted phenyl group or a naphthyl group. The compound as shown in the formula I is a tinib drug intermediate 6,7-disubstituted quinazolinone. According to the method provided in embodiments in the invention, aldoketones are used as cyclization raw materials in replacement of carboxylic acids for preparation of tinib drug intermediate, and since the aldoketones are not corrosive, the method has low requirements on reaction equipment and is more favorable for industrial production.

Description

technical field [0001] The present invention relates to the field of chemistry, in particular, the present invention relates to methods for preparing compounds. Background technique [0002] 6,7-disubstituted quinazolinone is a very important heterocyclic compound. Starting from this structure, a variety of tinib anticancer drugs can be effectively prepared, such as gefitinib, erlotinib, lapa Icotinib, Icotinib, and Vandetinib. There are many reports on the synthesis of quinazolinones containing substituents, but most of them use metal-catalyzed methods, which usually require toxic or difficult to handle oxidants. [0003] Furthermore, the process for preparing 6,7-disubstituted quinazolinones still needs further development and research. Contents of the invention [0004] The present invention aims to solve one of the technical problems in the related art at least to a certain extent. [0005] In the first aspect of the present invention, the present invention proposes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/88C07D239/94
CPCC07D239/88C07D239/94
Inventor 王立霞唐亚林胡本全
Owner INST OF CHEM CHINESE ACAD OF SCI
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