1429334-00-8

Basic information

• Product Name: AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-
• Synonyms: AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-;(S)-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)acetamide;N-[[(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-acetamide;Rivaroxaban AcetaMide Impurity;(S)-N-[{3-(4-(3-oxomorpholin-4-yl)phenyl)-2-oxo-1,3-oxazolidin-5-yl}methyl]acetamide
• CAS NO: 1429334-00-8
• Molecular Formula: C₁₆H₁₉N₃O₅
• Molecular Weight: 333.33916
• Mol File: 1429334-00-8.mol

Chemical Properties

• Boiling Point: 686.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.326±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 15.53±0.46(Predicted)
• CAS DataBase Reference: AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-(1429334-00-8)
• EPA Substance Registry System: AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]-(1429334-00-8)

Safety Data

• Hazardous Substances Data: 1429334-00-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
AcetaMide, N-[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]is used as an impurity in the development and production of Rivaroxaban, a novel antithrombotic agent. The presence of this compound in Rivaroxaban is essential for its function as a highly potent and selective, direct FXa inhibitor, which aids in the prevention and treatment of thrombotic disorders.
In the pharmaceutical industry, the compound is utilized to enhance the efficacy of Rivaroxaban as an antithrombotic agent. Its role in the development of this medication is significant, as it contributes to the overall effectiveness of the drug in treating and preventing thrombotic conditions.
Furthermore, the compound may also be used in research and development for the creation of new antithrombotic agents or for the improvement of existing ones. Its presence in Rivaroxaban provides valuable insights into the chemical properties and interactions that can be leveraged to develop more effective medications for thrombotic disorders.

Upstream product

• 1313613-18-1 [4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester 
• 183905-31-9 N-[(2S)-2-acetoxy-3-chloropropyl]acetamide 
• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 
• 898543-06-1 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one hydrochloride 
• 446292-10-0 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one 
• 75-36-5 acetyl chloride 
• 224323-47-1 (S)-N-(3-chloro-2-hydroxy-1-propyl)acetamide 
• 1429334-02-0 N-[(2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]acetamide 
• 530-62-1 1,1'-carbonyldiimidazole 
• 183805-10-9 N-[(2S)oxiranylmethyl]acetamide 

Downstream Products

• 446292-10-0 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one 

Relevant articles and documents

A related substance [...] F, G synthetic method

The invention provides synthetic methods of related substances F and G of rivaroxaban. With the adoption of the synthetic methods of the related substances F and G of the rivaroxaban, the yield is high, and industrial production and technology transformation are realized easily.

the advantage cuts down Sha Ban and intermediate preparation method

The present invention discloses a new method for preparing rivaroxaban through an intermediate represented by a formula (5), wherein the method comprises that: S-1-amino-3-chloro-2-propanol represented by a formula (2) is subjected to acylation modification to obtain a compound represented by a formula (3), the compound represented by the formula (3) reacts with 4-(3-oxomorpholineone)phenylamine formyl benzyl ester represented by a formula (4) under alkali catalysis so as to provide a structure represented by a formula (5) in a high yield manner, the intermediate is subjected to acid hydrolysis to prepare 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl-morpholin-3-one represented by a formula (6), and the 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl-morpholin-3-one reacts with 5-chlorothiophene-2-carbonyl chloride represented by a formula (c) to prepare the rivaroxaban. The rivaroxaban preparation method has advantages of high reaction yield, easy purification, mild reaction conditions, simple operation and the like, wherein the yield is significantly increased although acylation modification is required during the synthesis process, the purification process can be simplified, and the preparation method is suitable for industrial production.

PROCESSES FOR THE PREPARATION OF 5-CHLORO-N-({(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL) PHENYL]-1,3-OXAZOLIDIN-5-YL}METHYL)-2-THIOPHENE-CARBOXAMIDE AND INTERMEDIATES THEREOF

TThe present invention provides processes for the preparation of 5-chloro-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophene-carboxamide (I) and intermediates thereof. Also provides novel intermediates and their use in the synthesis of oxazolidine derivatives.