446292-08-6

Basic information

• Product Name: 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-
• Synonyms: 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-;4-[4-[(5S)-5-PhthaliMidoMethyl-2-oxo-3-oxazolidinyl]phenyl]-3-Morpholinone;2-[[(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole-1,3(2H)-dione;(S)-2-((2-oxo-3-(4-(3-oxoMorpholino)phenyl)oxazolidin-5-yl)Methyl)isoindoline-1,3-dione;2-({(5S)-2-oxo-3-[4-(3-oxoMorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}Methyl)-1H-isoindole-1,3(2H)-dione;RivaroxabanInterMediates-01;Rivaroxaban Intermediate5;Rivaroxaban Phthalimido Impurity
• CAS NO: 446292-08-6
• Molecular Formula: C₂₂H₁₉N₃O₆
• Molecular Weight: 421.407
• EINECS: 1806241-263-5
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Intermediate of Rivaroxaban
• Mol File: 446292-08-6.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 702.933 °C at 760 mmHg
• Flash Point: 378.92 °C
• Appearance: White solid
• Density: 1.466 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 0.99±0.20(Predicted)
• Water Solubility: 12mg/L at 20℃
• CAS DataBase Reference: 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-(446292-08-6)
• EPA Substance Registry System: 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-(446292-08-6)

Safety Data

• Hazardous Substances Data: 446292-08-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 446292-08-6 differently. You can refer to the following data:
1. 1H-isoindole-1,3(2H)-dione, 2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]- is an important intermediate for the synthesis of rivaroxaban, which is an anticoagulant and the first orally active direct factor Xa inhibitor.
2. Rivaroxaban intermediate.

Chemical Properties

White Solid

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C22H19N3O6/c26-19-13-30-10-9-23(19)14-5-7-15(8-6-14)24-11-16(31-22(24)29)12-25-20(27)17-3-1-2-4-18(17)21(25)28/h1-8,16H,9-13H2/t16-/m1/s1

Upstream product

• 161596-47-0 (S)-N-glycidylphthalimide 
• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 
• 1446022-14-5 butyric acid-2(R)-2-hydroxy-3-[4-(3-oxo-morpholin-4-yl)phenylamino]-propyl ester 
• 1446022-15-6 butyric acid-2-oxo-5(R)-3-[4-(3-oxomorpholin-4-yl)-phenyl]oxazolidin-5-yl-methyl ester 
• 1117893-60-3 4-{4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one 
• 136918-14-4 phthalimide 
• 1424942-80-2 (R)-(2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5-yl)methyl 4-methylbenzene sulfonate 
• 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 
• 1450876-94-4 2-((2R)-2-hydroxy-3-(N-(4-(3-oxomorpholin-4-yl)phenyl)-1H-imidazol-1-yl-carboxamido)propyl)-1H-isoindol-1,3(2H)-dione 
• 1325210-64-7 4-(4-isocyanatophenyl)morpholin-3-one 
• 1074-82-4 potassium phtalimide 
• 929281-94-7 (S)-4-(1,3-dioxoisoindol-2-yl)-3-hydroxybutyronitrile 
• 634905-12-7 4-(4-bromophenyl)morpholin-3-one 

Downstream Products

• 1446022-16-7 (S)-4-(4-(5-(aminomethyl)-2-oxo-oxazolidin-3-yl)phenyl)morpholin-3-one formate salt 
• 1446022-18-9 (S)-4-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one L-(+)-mandelate 
• 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 
• 366789-02-8 Rivaroxaban 
• 1415566-28-7 N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide 

Relevant articles and documents

Oxazolidinone derivative and preparation method thereof

The invention relates to a preparation method of an oxazolidinone compound impurity 5-chloro-nitrogen-[[(5S)-2-oxo-3-[4-acetamidophenyl]-1, 3- oxazolidine-5-yl]methyl] thiophene-2-methanamide (formulaI) in rivaroxaban. According to a preparation method, 4-aminoacetanilide (formula II) and (S)-N-epoxypropyl phthalimide (formula III) are used as raw materials, and the impurity is obtained through ring opening coupling, ring closing, protecting group removal and condensation reaction. The compound represented by formula I can be applied to rivaroxaban bulk drug quality control and qualitative and quantitative research and detection of impurities.

Preparation method of rivaroxaban intermediate

The invention provides a preparation method of a rivaroxaban intermediate. The preparation method comprises: (1) carrying out a reaction on a compound A and a compound B in an alcohol or an alcohol aqueous solution to obtain a compound C; and (2) reacting the compound C with N,N'-carbonyldiimidazole in a reaction solvent selected from acetonitrile or butyronitrile to obtain a reaction solution containing a compound D, and performing cooling crystallization to obtain a compound D.

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.