1796931-48-0

Basic information

• Product Name: Mirabegron Impurity
• Synonyms: (S)-Mirabegron;Mirabegron Impurity 1 ((S)-Mirabegron);2-(2-amino-1,3-thiazol-4-yl)-N-[4-[2-[[(2S)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]acetamide;(S)-2-(2-aminothiazol-4-yl)-N-(4-(2-((2-hydroxy-2-phenylethyl)amino)ethyl)phenyl)acetamide
• CAS NO: 1796931-48-0
• Molecular Formula: C21H24N4O2S
• Molecular Weight: 396.50586
• Mol File: 1796931-48-0.mol

Chemical Properties

• Boiling Point: 690.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.313±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.51±0.70(Predicted)
• CAS DataBase Reference: Mirabegron Impurity(CAS DataBase Reference)
• NIST Chemistry Reference: Mirabegron Impurity(1796931-48-0)
• EPA Substance Registry System: Mirabegron Impurity(1796931-48-0)

Safety Data

• Hazardous Substances Data: 1796931-48-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Mirabegron Impurity is used as a reference material for quality control and analytical testing in the pharmaceutical industry. It helps ensure the purity and efficacy of Mirabegron, a potent bladder relaxant and reagent for diabetes remedy, by providing a benchmark for comparison during the synthesis or manufacturing process.
Used in Research and Development:
Mirabegron Impurity is used as a research tool in the development of new drugs and therapies for bladder and diabetes-related conditions. It aids scientists in understanding the structure, properties, and potential interactions of Mirabegron and its impurities, which can contribute to the discovery of more effective and safer treatments.

Upstream product

• 24954-67-4 2-(p-nitrophenyl)ethylamine 
• 20780-53-4 (R)-Styrene oxide 
• 29968-78-3 2-(4-nitrophenyl)ethylamine monohydrochloride 
• 556-18-3 4-aminobenzaldehyde 
• 89336-46-9 2-{2[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl}acetic acid 
• 1460-05-5 p-nitrophenylacetaldehyde 
• 94838-59-2 tert-butyl 4-aminophenethylcarbamate 
• 13472-00-9 p-Aminophenethylamine 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 29676-71-9 2-amino-4-thiazoleacetic acid 
• 521284-19-5 (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide 
• 611-71-2 (R)-Mandelic Acid 

Downstream Products

• 391901-45-4 YM-208876 
• 1365244-68-3 YM-554028 
• 1365244-67-2 YM-538859 

Relevant articles and documents

Preparation method of mirabegron key intermediate

The invention provides a preparation method of a mirabegron key intermediate, namely, a compound as shown in a formula (III). The method is simple, convenient and safe to operate, free of harsh reaction conditions, high in reaction purity and yield and low in process cost which is about 40% of that of a process using a metal catalyst such as palladium carbon, is suitable for large-scale production and conforms to the green chemistry principle. A finished product of mirabegron continues to be prepared by using the intermediate compound as shown in the formula (III) prepared by the method so as to meet the existing requirements.

A new process for the preparation of (R)-2-((4-Aminophenethyl)amino)-1-phenylethanol

The present invention relates to a process for the preparation (R)-2 - ((4-aminophenethyl) amino) -1 - phenylethanol, which is an intermediate of mirabberone intermediate. A manufacturing method of a high purity and high yield amide derivative is provided to produce an amide derivative having high purity and high yield without using a specific purification process by using a zinc powder reduction catalyst.

Preparation method of mirabegron (by machine translation)

The method is convenient to operate, controllable in reaction process, high in 2 - final product purity,4 - high in yield and suitable for industrial production, so that a more valuable synthesis route is provided for preparing mirabead, good social benefits and economic benefits can be brought, and the economic value potential is great. (by machine translation)

Mirabegron impurity compound, and preparation method and application thereof

The invention discloses a mirabegron impurity compound, and a preparation method and application thereof. The mirabegron impurity compound disclosed by the invention is relatively high in purity and can be used as a reference substance for effectively identifying impurities generated in mirabegron synthesis, so that the drug quality of mirabegron is controlled.

Preparation method of mirabegron

The invention discloses a preparation method of mirabegron, and the method comprises: S1, carrying out reduction reaction on p-nitrophenylacetonitrile to obtain p-nitrophenylacetaldehyde; S2, carryingout condensation reduction on the p-nitrophenylacetaldehyde and (R) 2-amino-1-phenethyl alcohol to obtain (R) 2-(4-nitrophenethyl) amino)-1-phenyl ethyl alcohol; S3, carrying out reduction on the (R)2-amino-1-phenethyl alcohol to obtain (R) 2-(4-nitrophenethyl) amino)-1-phenyl ethyl alcohol to obtain an intermediate (R) 2-((4-aminophenyl ethyl) amino)-1-phenyl ethyl alcohol; and S4, carrying outcondensation on the (R) 2-((4-aminophenyl ethyl) amino)-1-phenyl ethyl alcohol and aminothiazole acetic acid to obtain the mirabegron. According to the method, the starting raw materials are cheap and easy to obtain, the reaction conditions are controllable, the synthetic route steps are few, the yield is high, the cost is low, and the prepared mirabegron is high in purity.

Salts of amide derivatives and method for preparing the same

In the present invention, a cyclised amino acid is disclosed as an aliphatic or aromatic disulfonate or lactam structure, which is a salt of an amide derivative represented by chemical formula 1. The salt of the amide derivative does not absorb moisture, and is stable and has excellent solubility in water. In chemical formula 1, the B ring is a substituted or unsubstituted heteroaryl group, X is a bond, hydroxy, lower alkylene, lower alkenylene, carbonyl or -NH-, and A is lower alkylene or -lower alkylene-O-.COPYRIGHT KIPO 2019

Method for preparing amide derivatives

Disclosed in the present specification is a method for producing amide derivatives of chemical formula 1. The method comprises the steps of: conducting a reaction of chemical formula 2 and chemical formula 3; and reacting chemical formula 4 with a compound produced by the reaction. By using the method disclosed in the present specification, it is possible to exclude a hydrogenation reaction which is limited by high production cost and low production yield in on-site production.COPYRIGHT KIPO 2018

Synthetic method of the compound

A synthesis method of a compound shown as a formula 1 is provided. The method includes (1) bringing a compound shown as a formula 2 into contact with compound shown as a formula 3 to produce a compound shown as a formula 4; (2) subjecting nitro of the compound shown as the formula 4 to a reduction reaction to produce a compound shown as a formula 5; and (3) bringing the compound shown as the formula 5 into contact with a compound shown as a formula 6 to produce the compound shown as the formula 1. The method is short in route. Initial raw materials are cheap and easily available. All the intermediates are easy to purify and simple in after-treatment. The product is high in purity and high in yield. The method benefits industrial production.

First Direct Isolation of Stable α-Form Crystals of Mirabegron, a Selective β3-Adrenoceptor Agonist

An efficient and scalable method for the direct isolation of stable α-form crystals of Mirabegron (1) is developed. The developed method negates transformation of metastable β-form crystals into α-form crystals thereby overcoming the limitations of reported methods and avoids additional processing steps during its manufacture. The developed method directly provides stable α-form crystals of Mirabegron (1) with yield of around 84% and purity of >99.77% by HPLC in a single step.

Study on a New Method for Synthesis of Mirabegron

Mirabegron is a muscle relaxing drug for the treatment of overactive bladder. The existing synthetic methods for mirabegron produced intermediate product 4-(2-(phenethylamino)ethyl)aniline, which complicated the final product purification process. In this study, we designed a new synthetic route for mirabegron with low cost starting materials and a production of mirabegron at a 99.6% purity and a 61% overall yield. Particularly, this new synthetic route did not produce side product 4-(2-(phenethylamino)ethyl)aniline, which significantly simplified the product purification process.