147404-76-0

Basic information

• Product Name: Azilsartan iMpurity A
• Synonyms: Azilsartan iMpurity A;Methyl 1-((2'-carboxaMidebiphenyl-4-yl) Methyl)-2-ethoxy-1H-benziMidazole-7-carboxylate;ethyl 1-((2'-carboxaMidebiphenyl-4-yl) Methyl)-2-ethoxy-1H-benziMidazole-7-carboxylate;1-((2'-carboxaMidebiphenyl-4-yl) Methyl)-2-ethoxy-1H-benziMidazole-7- carboxylic acid;Methyl 1-[((2'-(2,5-dihydro-5-oxo-1,2,4- xadiazol-3-yl)biphenyl)-4-yl)Methyl]-2H-benziMidazol-2-one -7- carboxylate;Ethyl 1-[((2'-(2,5-dihydro-5-oxo-1,2,4- xadiazol-3-yl)biphenyl)-4-yl)Methyl]-2H-benziMidazol-2-one -7- carboxylate;1-[[2'-(Aminocarbonyl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid methyl ester;methyl 1-((2'-carbamoyl-[1,1'-biphenyl] -4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate
• CAS NO: 147404-76-0
• Molecular Formula: C₂₅H₂₃N₃O₄
• Molecular Weight: 429.46782
• Mol File: 147404-76-0.mol

Chemical Properties

• Boiling Point: 652.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• PKA: 15.84±0.50(Predicted)
• CAS DataBase Reference: Azilsartan iMpurity A(CAS DataBase Reference)
• NIST Chemistry Reference: Azilsartan iMpurity A(147404-76-0)
• EPA Substance Registry System: Azilsartan iMpurity A(147404-76-0)

Safety Data

• Hazardous Substances Data: 147404-76-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Manufacturing:
Azilsartan iMpurity A is used as a quality control parameter in the production of azilsartan for high blood pressure treatment. It is crucial for ensuring the safety and effectiveness of the medication by being accurately identified and quantified.
Used in Regulatory Compliance:
Azilsartan iMpurity A is used as a benchmark for regulatory authorities to set specific limits on the presence of this impurity in the final drug product. This ensures the safety of the medication for human consumption and adherence to pharmaceutical standards.
Used in Research and Development:
Azilsartan iMpurity A is utilized in research to understand its formation mechanisms during the synthesis process and to develop methods for its reduction or elimination, thereby improving the overall quality of the drug azilsartan.
Used in Analytical Chemistry:
Azilsartan iMpurity A serves as a subject for analytical methods development, where techniques such as chromatography, mass spectrometry, and spectrophotometry are employed to detect and quantify its presence in the drug product, aiding in the strict quality control measures required in pharmaceutical production.

Upstream product

• 139481-44-0 methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate 
• 147403-65-4 methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate 

Downstream Products

• 1696392-11-6 1-((2’-carbamoyl-[1,1’-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylic acid 

Relevant articles and documents

A process for the preparation of intermediates arab League Qi Shatan

The invention discloses a preparation method of an azilsartan intermediate. The preparation method of the azilsartan intermediate comprises the following steps: dissociating hydroxylamine hydrochloride through alkali in ethanol which is 90-95% in mass percentage, filtering, adding a compound as shown in formula (II) in the specification, triethylamine and ethanol to filtrate, implementing a reflux reaction, cooling and crystallizing after the reaction, and filtering to obtain the target intermediate as shown in formula (I). The target intermediate prepared by the preparation method disclosed by the invention is high in content, and low in content of amide impurities, which is generally less than 10%.

Aitch sand smooth process for the preparation of intermediates

The invention relates to the technical field of azilsartan intermediate preparation method. According to the invention, a compound 1-[(2'-cyanobiphenyl-4-group)methyl]-2-ethoxy benzimidazole-7-methyl carboxylate is subject to a reaction with an aqueous solution of hydroxylamine, such that the intermediate is prepared. In prior arts, amide impurities with an amount equal to that of the products are generated. With the method provided by the invention, the impurities are greatly reduced, such that the yield is increased. In prior arts, the reaction time is 48 hours, and yet a small amount of raw materials is not reacted. With the method provided by the invention, the reaction time is 24 hours, and the reaction is sufficiently carried out, such that the efficiency is improved. In a post-processing process, complicated steps of acid extraction and alkali ionization are not required. When the reaction id finished, the materials are cooled, and the target product can be precipitated directly.

Aitch sand smooth intermediate and its preparation method (by machine translation)

The invention discloses Aitch sand smooth intermediate and its preparation method. The preparation method comprises the following steps: in the solvent, compound 2B with hydroxylamine mixing, reaction, get compound 3B can be. The invention method for preparing the Aitch of less impurity, short reaction time, the higher process yield, high purity of the product, is suitable for industrial production. (by machine translation)

Aitch sand smooth intermediate and its and Aitch of preparation method

The invention discloses a preparation method of an intermediate 5B and azilsartan 1. The preparation method of the azilsartan 1 comprises the following steps: 1) in a solvent, mixing a compound 2B with hydroxylamine to react to obtain a compound 3B; 2) in a solvent, mixing the compound 3B prepared in the step 1) with chloroformate to react under the action of alkali to obtain a compound 4B; 3) in a solvent, carrying out cyclization reaction on the compound 4B prepared in the step 2) to obtain a compound 5B; and 4) in a solvent, carrying out esterolysis reaction on the compound 5B prepared in the step 3) under the action of alkali to obtain the azilsartan 1, wherein R is a C6-C10 aryl group or C1-C4 straight-chain or branched-chain alkyl group. The preparation method of the azilsartan intermediate 5B is described as the step 3). The preparation method has the advantages of fewer impurities, short reaction time, higher technical yield and higher product purity, and is suitable for industrial production.

Commercial synthesis of azilsartan kamedoxomil: An angiotensin II receptor blocker

A commercially viable process for the preparation of azilsartan kamedoxomil, an angiotensin II receptor blocker, has been developed. The present work describes the novel synthesis of azilsartan medoxomil from amidoxime methyl ester. The present work also describes the improved synthesis of amidoxime methyl ester and azilsartan kamedoxomil. This process features a high overall yield (36%) with 99.52% HPLC purity.