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Preparation method of linagliptin, a medicine for treating diabetes

A synthesis method and compound technology are applied in the field of preparation of the drug linagliptin, and can solve the tedious reaction route of linagliptin, the tedious preparation process of intermediate 2-chloromethyl-4-methylquinazoline, and the replacement of linagliptin. The problems of low reaction yield, etc., are easy to operate, beneficial to industrial production, and the reaction route is short.

Active Publication Date: 2020-10-09
深圳市福宏生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The technical problem to be solved in the present invention is aimed at the problems in the prior art that the reaction route of linagliptin is relatively cumbersome, the preparation process of the intermediate 2-chloromethyl-4-methylquinazoline is lengthy, and the yield of the subsequent substitution reaction is low.

Method used

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  • Preparation method of linagliptin, a medicine for treating diabetes
  • Preparation method of linagliptin, a medicine for treating diabetes
  • Preparation method of linagliptin, a medicine for treating diabetes

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preparation example Construction

[0027] The invention discloses a preparation method of linagliptin, and those skilled in the art can learn from the content of this article and appropriately improve the process parameters to realize it. It needs to be pointed out that all similar replacements and modifications are obvious to those skilled in the art, and they are all considered to be included in the present invention, and relevant personnel can obviously make changes without departing from the content, spirit and scope of the present invention. Changes or appropriate changes and combinations are made to the content described herein to realize and apply the technology of the present invention.

[0028] In the present invention, unless otherwise specified, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art.

Embodiment 1

[0030] Embodiment 1: the preparation of 2-chloromethyl-4-methylquinazoline

[0031]

[0032] In 150mL tetrahydrofuran, add 6.05g (45mmol) o-aminoacetophenone and 4.68g (50mmol) 2-chloroacetamide, in the presence of 0.45g (4.5mmol) catalyst cuprous chloride and 9.11g (90mmol) triethylamine Under reflux, feed oxygen, stir under reflux for 12 hours, TLC monitors the reaction progress, treats that reaction completes, removes solvent under reduced pressure, through column chromatography, obtains compound 2-chloromethyl-4-methylquinazoline 7.61g (39.5 mmol), the yield was 88%.

Embodiment 2

[0033] Embodiment 2: the preparation of 2-bromomethyl-4-methylquinazoline

[0034]

[0035] In 150mL tetrahydrofuran, add 6.05g (45mmol) o-aminoacetophenone and 6.62g (48mmol) 2-bromoacetamide, in the presence of 0.45g (4.5mmol) catalyst cuprous chloride and 12.44g (90mmol) potassium carbonate , feed into oxygen, stir under reflux for 12 hours, TLC monitors the reaction process, after the reaction is completed, filter, remove the solvent under reduced pressure, and obtain compound 2-bromomethyl-4-methylquinazoline 9.72g through column chromatography ( 41 mmol), the yield was 91%.

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Abstract

The invention provides a preparation method of linagliptin. The preparation method comprises the following steps: in the presence of cuprous chloride catalyst, cyclizing 2-aminoacetophenone and a corresponding amide, which are taken as starting materials, to obtain a quinazoline compound; and in addition, sulfonyl is easier to remove compared with halogen, and is introduced into reaction raw materials, sulfonyl is easier to be replaced in subsequent substitution reaction, and a high-yield coupling product is obtained. The method has the advantages of short reaction route, high yield and few byproducts, lowers the production cost, and is beneficial to industrial production.

Description

technical field [0001] The application relates to a preparation method of linagliptin, a medicine for treating diabetes, and belongs to the field of western medicine synthesis. Background technique [0002] In recent years, the incidence of diabetes has increased year by year, and diabetes has become another non-communicable disease that seriously threatens human health after cardiovascular diseases and malignant tumors. The type II incidence of diabetes accounts for 90%, and the pathogenesis of type II diabetes is mainly caused by the human body's resistance to insulin and insulin and cell function defects. Clinically used drugs for the treatment of type II diabetes mainly include insulin secretion promoters, sulfonylureas, meglitinides, insulin sensitizers, insulin and insulin receptor agonists and dipeptidyl peptidase-4 inhibitors . [0003] Linagliptin (linagliptin), the chemical name is 8-[(3R)-3-amino-1-piperidinyl]-7-(2-butynyl)-3,7-dihydro-3-methyl -1-[(4-Methyl-2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/04
CPCC07D473/04
Inventor 陈旭红谭回阎德文李海燕刘雪婷欧慧婷蔡金霖
Owner 深圳市福宏生物科技有限公司
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