1411775-06-8

Basic information

• Product Name: Rivaroxaban Impurity 11
• Synonyms: Rivaroxaban Impurity 11;Rivaroxaban Impurity 29;Rivaroxaban Impurity 46
• CAS NO: 1411775-06-8
• Molecular Formula: C14H17N3O4
• Molecular Weight: 291.30248
• Mol File: 1411775-06-8.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 580.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.348±0.06 g/cm3(Predicted)
• PKA: 8.96±0.29(Predicted)
• CAS DataBase Reference: Rivaroxaban Impurity 11(CAS DataBase Reference)
• NIST Chemistry Reference: Rivaroxaban Impurity 11(1411775-06-8)
• EPA Substance Registry System: Rivaroxaban Impurity 11(1411775-06-8)

Safety Data

• Hazardous Substances Data: 1411775-06-8(Hazardous Substances Data)

Usage

General Description

Rivaroxaban Impurity 11 is a chemical substance that is classified as an impurity and is associated with the anticoagulant drug rivaroxaban. It is used as a reference standard in the pharmaceutical industry for quality control and testing purposes. This impurity may be present in small amounts in rivaroxaban formulations and it is necessary to monitor its levels to ensure the safety and effectiveness of the drug. The presence of impurities such as Rivaroxaban Impurity 11 can affect the purity and stability of the drug, potentially impacting its therapeutic properties. Therefore, it is important to closely monitor and control the levels of this impurity in rivaroxaban formulations.

Upstream product

• 1424944-35-3 2-({2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione 
• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 
• 1411711-56-2 4-{4-[5-chloromethyl-2-oxo-1,3-oxazoIidine-3-yl]-phenyl}-morpholine-3-one 
• 1411711-52-8 (dl)-4-[4-[(3-chloro-2-hydroxypropyl)amino]phenyl]-3-morpholinone 
• 1411711-66-4 4-{4-[5-aminomethyI-2-oxo-1,3-oxazolidine-3-yl]-phenyl}-morphoIine-3-one acetate 
• 1411711-60-8 4-{4-[5-iodomethyl-2-oxo-1,3-oxazolidine-3-yl]-phenyl}-morpholine-3-one 
• 1411775-03-5 4-{4-[5-[(dibenzylamino)methyl]-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholine-3-one 
• 1424944-35-3 2-({(5R)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione 
• 446292-08-6 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione 
• 74-89-5 methylamine 
• 446292-07-5 2-((2S)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 366789-02-8 Rivaroxaban 
• 482306-32-1 5-chloro-N-({(5)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophenecarboxamide 
• 1415566-28-7 N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide 
• 1616563-62-2 N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)formamide 
• 1616563-61-1 5-chloro-N-formyl-N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide 

Relevant articles and documents

Identification and Synthesis of Impurities During a Novel Process Development of Rivaroxaban

During the development of rivaroxaban, seven process-related impurities have been identified and synthesized. These structures are confirmed by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The impurities (S)-2-(2-((4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)amino)ethoxy)acetohydrazide (A) and (S)-4-(4-(((2-oxooxazolidin-5-yl)methyl)amino)phenyl)morpholin-3-one (F) are confirmed and distinguished from their isomers by single-crystal diffraction. This work proves to be valuable in regard to complying with regulatory norms and assessing the quality of rivaroxaban.

Synthesis method of rivaroxaban

The invention discloses a synthetic method of rivaroxaban. According to the method, rivaroxaban is prepared by adopting a one-pot method; 2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindol-1,3(2H)-one in an alcohol solvent is subjected to an ammonolysis reaction in the presence of an alkali to remove a protective group, then to evaporation to remove the alcohol solvent, and finally to condensation with 5-chlorothiophene-2-formyl chloride under the action of an acid-binding agent, wherein the reaction alcohol solvent is alcohol with a carbon number of 4 or below, the alkali is an organic alkali or inorganic alkali, a condensation reaction solvent is water, and the acid-binding agent is potassium carbonate or sodium carbonate. The method has the advantages ofmild reaction conditions, simple post-treatment, conservation of a large amount of manpower and material resources, and applicability to large-scale industrial production.

A [...] synthesis process

The invention relates to the technical field of heterocyclic chemistry, specifically to the technical field of nitrogen-oxygen heterocyclic chemistry. Specifically speaking, the invention discloses a novel synthetic process for rivaroxaban. According to the process, the R group of a compound with a structure as shown in a formula (I) is removed so as to obtain a compound with a structure as shown in a formula (II) or an acid salt thereof, and the compound with the structure as shown in the formula (II) or the acid salt thereof reacts with a compound with a structure as shown in a formula (III) under the action of alkali so as to prepare rivaroxaban, wherein the formulas are described in the specification, and R in the formulas is a C1-20 aliphatic/aromatic hydrocarbon group.