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Synthesis method of tegoprazan

A synthetic method, Tego's technology, applied in the field of organic synthesis of drugs, can solve the problems of high cost and low yield, and achieve the effects of less by-products, high reaction selectivity, and high reaction yield

Pending Publication Date: 2021-10-22
西安淳甄新材料有限公司
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Problems solved by technology

Based on the description of the above patent, the preparation of Tegoprazan mainly involves 4-hydroxy-N,N,2-trimethyl-1-[(4-tolyl)sulfonyl]-1H-benzimidazole-6-carboxamide and Condensation of (S)-5,7-difluoro-3,4-dihydro-2H-chromen-4-ol, which not only involves the use of dangerous reagents tributylphosphine and azo compounds , and the yield is lower and the cost is higher

Method used

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  • Synthesis method of tegoprazan
  • Synthesis method of tegoprazan
  • Synthesis method of tegoprazan

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preparation example Construction

[0047] The present invention proposes a new method for preparing tergrazan, involving 4-hydroxy-N,N,2-trimethyl-1H-benzimidazole-6-carboxamide (stage A), (S)-5 , Preparation of 7-difluoro-3,4-dihydro-2H-chromen-4-ol (stage B), and finally the Mitsunobu reaction.

[0048] The present invention adopts starting material 2-amino-3-nitrophenol to prepare compound A8 through a step-by-step reaction. First, 2-amino-3-nitrophenol and benzyl bromide form ether to prepare compound A1; compound A1 and n -Bromosuccinimide undergoes a bromination reaction to generate compound A2; the amino group of compound A2 reacts with acetic anhydride to generate compound A3; compound A3 undergoes reduction and cyclization with a reducing agent to generate compound A4; after forming a ring, In order to improve the reaction selectivity and reaction yield, the nitrogen of the benzimidazole ring in compound A4 is protected by benzyl bromide or benzyl chloride to generate compound A5; then the aryl bromide...

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Abstract

The invention discloses a synthesis method of tegoprazan, the method comprises the following steps: preparing 4-hydroxy-N, N, 2-trimethyl-1H-benzimidazole-6-formamide, preparing (S)-5, 7-difluoro-3, 4-dihydro-2H-chromene-4-alcohol, and finally carrying out Mitsunobu reaction: carrying out Mitsunobu reaction under the action of a phosphine reagent and a condensing agent to prepare the tegoprazan: (s)-4-((5, 7-difluorochroman-4-yl) oxy)-i n, n, 2-trimethyl-1h-benzimidazole-i-6-carboxamide. The tegoprazan is prepared through step-by-step reaction, the reaction selectivity is high, the yield is high, and the method is environmentally friendly and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis of medicines and relates to a synthesis method of tegrazan. Background technique [0002] Tegorazan, also known as tegoprazan, tegoprazan, cj-12420, was approved for marketing by the Korean Ministry of Food and Drug Safety (MFDS) in July 2018, for the treatment of gastroesophageal reflux disease and erosive esophagitis . Tegoprazan is a competitive potassium ion acid blocker (p-cab) and hydrogen ion / potassium ion exchange ATPase (h+ / k+atpase) inhibitor, which has a fast onset of action and can control the pH value of gastric juice for a long time. A new drug for the treatment of gastroesophageal reflux disease and erosive esophagitis. [0003] The chemical name of Tegoprazan is (s)-4-((5,7-difluorochroman-4-yl)oxy)-n,n,2-trimethyl-1h-benzimidazole- 6-formamide, the chemical structure contains a benzimidazole structure and a chiral 5,7-difluorochroman-4-oxyl structure. The preparation of tergra...

Claims

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Application Information

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IPC IPC(8): C07D405/12
CPCC07D405/12C07B2200/07Y02P20/55
Inventor 谢卓桐方勇闫路吴阳梁腾张森
Owner 西安淳甄新材料有限公司
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