721401-53-2

Basic information

• Product Name: 2-ThiophenecarboxaMide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-Morpholinyl)phenyl]aMino]propyl]-
• Synonyms: 2-ThiophenecarboxaMide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-Morpholinyl)phenyl]aMino]propyl]-;Decarbonyl Rivaroxaban;Imp. G:5-chloro-N-((2R)-2-hydroxy-3-{[4-(3-oxo-4-morpholinyl)-phenyl]amino}propyl)-2-thiophenecarboxamide;(R)-5-Chloro-N-(2-hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)thiophene-2-carboxamide;Rivaroxaban impurity P4D-P
• CAS NO: 721401-53-2
• Molecular Formula: C₁₈H₂₀ClN₃O₄S
• Molecular Weight: 409.8871
• EINECS: -0
• Mol File: 721401-53-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 772.6±60.0 °C(Predicted)
• Appearance: /
• Density: 1.434±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.65±0.46(Predicted)
• CAS DataBase Reference: 2-ThiophenecarboxaMide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-Morpholinyl)phenyl]aMino]propyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ThiophenecarboxaMide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-Morpholinyl)phenyl]aMino]propyl]-(721401-53-2)
• EPA Substance Registry System: 2-ThiophenecarboxaMide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-Morpholinyl)phenyl]aMino]propyl]-(721401-53-2)

Safety Data

• Hazardous Substances Data: 721401-53-2(Hazardous Substances Data)

Usage

Description

2-Thiophenecarboxamide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-morpholinyl)phenyl]amino]propyl]is a complex organic compound with a unique chemical structure. It is characterized by the presence of a thiophene ring, a carboxamide group, a chloro substituent, and a hydroxyl group attached to a chiral carbon center. 2-ThiophenecarboxaMide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-Morpholinyl)phenyl]aMino]propyl]has the potential for various applications in different industries due to its diverse functional groups and structural features.

Uses

Used in Pharmaceutical Industry:
2-Thiophenecarboxamide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-morpholinyl)phenyl]amino]propyl]is used as a potential therapeutic agent for the treatment of various diseases. Its unique chemical structure allows it to interact with specific biological targets, such as enzymes or receptors, which can lead to the modulation of cellular processes and the amelioration of disease symptoms.
Used in Chemical Synthesis:
2-ThiophenecarboxaMide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-Morpholinyl)phenyl]aMino]propyl]can be used as a building block or intermediate in the synthesis of more complex molecules with specific applications. Its diverse functional groups make it a versatile starting material for the development of new drugs, agrochemicals, or other specialty chemicals.
Used in Material Science:
The unique structural features of 2-Thiophenecarboxamide, 5-chloro-N-[(2R)-2-hydroxy-3-[[4-(3-oxo-4-morpholinyl)phenyl]amino]propyl]may also find applications in the development of new materials with specific properties. For example, it could be used to create novel polymers, coatings, or other materials with tailored characteristics for various industrial applications.
Used in Research and Development:
Due to its complex structure and potential for various applications, this compound can be a valuable tool in research and development. It can be used to study the effects of different functional groups and structural features on the properties and activities of molecules, which can provide valuable insights for the design of new compounds with specific applications.

Upstream product

• 366789-02-8 Rivaroxaban 
• 446292-04-2 4-(4-nitrophenyl)-3-morpholinone 
• 29518-11-4 4-phenylmorpholin-3-one 
• 62-53-3 aniline 
• 122-98-5 2-Anilinoethanol 
• 22353-82-8 5-chlorothiophene-2-carboxamide 
• 35475-03-7 methyl 5-chloro-2-thiophenecarboxylate 
• 1403383-56-1 (S)-4-[4-[(3-amino-2-hydroxypropyl)amino]phenyl]-3-morpholinone 
• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 1384257-81-1 N-[(2S)-3-chloro-2-hydroxypropyl]-5-chlorothiophene-2-carboxamide 
• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 
• 1252018-10-2 4-[4-(N-(3-chloro-(2R)-2-hydroxy-1-propyl)amino)phenyl]morpholin-3-one 
• 1325210-61-4 5-chloro-thiophene-2-carboxylic acid (S)-2-hydroxy-3-tosyloxy-propyl-amide 

Downstream Products

• 913565-18-1 5-Chloro-N-({(5S)-2-imino-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-thiophene-2-carboxamide 
• 366789-02-8 Rivaroxaban 

Relevant articles and documents

Hydrolytic degradation study of rivaroxaban: Degradant products identification by LC-MS isolation by Prep-HPLC and characterization by HRMS, NMR and FT-IR

Present work illustrates the stress degradation behaviour of rivaroxaban under hydrolytic, oxidative, thermal and photolytic conditions as per ICH guidelines. Under thermal and photolytic conditions drug had a fair stability where as in other stress conditions degradation products were observed. Initial identification of the degradation products was performed by hyphenated mass spectrometry coupled to ultra-performance liquid chromatography (UPLC-MS) and mass directed auto purification (MDAP) was used for isolation. Various 1D and 2D nuclear magnetic resonance (NMR) were performed to characterize the degradation products which were assisted by FT-IR and HRMS data. Two novel degradant products were observed in hydrolytic conditions, isolated and characterized by spectroscopic techniques as (R)-2-(2-((4-((3-(5-chlorothiophene-2-carboxamido)-2-hydroxypropyl)amino)phenyl)amino)ethoxy)acetic acid (DP-2) (m.w. of 427.90 g/mol and m.f. C18H22N3O5SCl), and 5-chlorothiophene-2-carboxylic acid (DP-3) (m.w. 161.95 g/mol and m.f. C5H3O2SCl). Additionally, two more degradation products were observed in basic and acidic conditions, viz. (R)-5-chloro-N-(2-hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)thiophene-2-carboxamide (DP-1) (m.w. 409.09 g/mol and m.f. C18H20N3O4SCl) and (S)-2-(2-((4-(5-((5-chlorothiophene-2-carboxamido)methyl)-2-oxooxazolidin-3-yl)phenyl)amino)ethoxy)acetic acid (DP-4) (m.w. 453.08g /mol and m.f. C19H20N3O6SCl) are already reported.

Rivaroxaban thiophene carboxylate impurity reference substance and preparation method thereof

The invention discloses a synthesis method of a rivaroxaban thiophene carboxylate impurity. The full name of the impurity is: 1-amino-3 ((4-(3-oxomorpholino) phenyl) amino) prop-2-yl 5-chlorothiophene-2-carboxylic acid ethyl ester hydrochloride. The invention also discloses a preparation method of the rivaroxaban thiophene carboxylate impurity. The preparation method comprises the following steps:dissolving rivaroxaban oxazolidine in an organic solvent, carrying out ring opening under the action of an acidic solution to obtain a rivaroxaban thiophene carboxylate impurity crude product, and recrystallizing with the organic solvent to obtain the high-purity rivaroxaban thiophene carboxylate impurity reference substance. The rivaroxaban thiophene carboxylate impurity is simple in preparationprocess and high in purity, and a qualified rivaroxaban thiophene carboxylate impurity reference substance can be provided for quality control of rivaroxaban.

A method for preparing the advantage cuts down Sha Ban

The invention discloses a preparation method of rivaroxaban, belonging to the field of chemical synthesis of medicine. The preparation method of rivaroxaban comprises the following steps: reacting 5-chlorothiophene-2-carboxylic acid-[(s)-2,3-dyhydroxy propyl]-amide with iodine under the catalytic action of triphenylphosphine and imidazole to produce 5-chlorothiophene-2-carboxylic acid-[(s)-3-iodo-2-hydroxy propyl]-amide; then reacting 5-chlorothiophene-2-carboxylic acid-[(s)-3-iodo-2-hydroxy propyl]-amide with 4-(4-aminophenyl)-3-morpholinone to produce 5-chlorothiophene-2-carboxylic acid{(R)-2-hydroxy-3-[4-(3-oxomorpholine-4-yl) phenyl amino]-propyl} amide; and finally introducing CO2 to react to produce rivaroxaban. The preparation method provided by the invention has the advantages that expensive and poisonous raw materials are not used, the production cost is low, the production safety is high, the environment pollution is hardly caused. Therefore, the preparation method is suitable for industrial production.