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

• 721401-52-1 (S)-N-(3-bromo-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide 
• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 
• 348626-26-6 5-chloro-N-(oxiran-2-ylmethyl)thiophene-2-carboxamide 
• 71-36-3 butan-1-ol 
• 799012-78-5 5-chloro-N-{[(2S)-oxiran-2-yl]methyl}thiophene-2-carboxamide 
• 1325210-61-4 5-chloro-thiophene-2-carboxylic acid (S)-2-hydroxy-3-tosyloxy-propyl-amide 
• 1325210-64-7 4-(4-isocyanatophenyl)morpholin-3-one 
• 721401-51-0 5-chlorothiophene-2-carboxylic acid [(S)-2,3-dihydroxypropyl]amide 
• 1252018-10-2 4-[4-(N-(3-chloro-(2R)-2-hydroxy-1-propyl)amino)phenyl]morpholin-3-one 
• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 
• 1384257-81-1 N-[(2S)-3-chloro-2-hydroxypropyl]-5-chlorothiophene-2-carboxamide 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 35475-03-7 methyl 5-chloro-2-thiophenecarboxylate 
• 1403383-56-1 (S)-4-[4-[(3-amino-2-hydroxypropyl)amino]phenyl]-3-morpholinone 

Downstream Products

• 366789-02-8 Rivaroxaban 
• 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 

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.

Method for preparing rivaroxaban intermediate and method for preparing rivaroxaban from rivaroxaban intermediate

The invention provides a method for preparing a rivaroxaban intermediate shown as a formula (VI) and a method for preparing rivaroxaban. The preparation method of the intermediate has the advantages of simple steps, easily controlled conditions, good selectivity, high yield, few impurities and the like, and green synthesis of rivaroxaban can be realized.

A oxazolidinone compounds of preparation method

The invention discloses a method for preparing an oxazolidinone compound. The method comprises the following steps of carrying out ammonolysis reaction on a racemic or optically active 3-chloro-2-hydroxypropyl aniline compound (2) as a starting material and ammonia in a proper solvent and under alkaline condition to obtain a 3-amino-2-hydroxypropyl aniline compound (3); carrying out acylation reaction on the compound (3) to obtain 3-acylamino-2-hydroxypropyl aniline compound (4); and carrying out cyclization reaction on the compound (4) and a corresponding acylating reagent to obtain the racemic or optically active oxazolidinone compound (II) as shown in the description, wherein R1 represents morpholinyl or 3-oxo-4-morpholinyl; R2 represents H or F; and R3 represents C1-12 alkyl, 5-chloro-thiophen-2-yl, thiophen-2-yl or 4,5-dichloro-2-yl; and the compound is a racemate and (S)- or (R)- optical isomers.