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

Description

1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]is a complex organic compound characterized by its unique molecular structure. It is a white solid and serves as a crucial intermediate in the synthesis of various pharmaceutical compounds, particularly rivaroxaban.

Uses

Used in Pharmaceutical Industry:
1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]is used as a key intermediate in the synthesis of rivaroxaban, an anticoagulant medication. Rivaroxaban is the first orally active direct factor Xa inhibitor, which plays a significant role in the coagulation cascade and is essential for the prevention and treatment of blood clot-related disorders.
Used as Rivaroxaban Intermediate:
1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]is specifically utilized in the production of rivaroxaban, which is a vital drug in the prevention and treatment of various blood clot-related conditions, such as deep vein thrombosis, pulmonary embolism, and stroke. Its role as an intermediate in the synthesis of rivaroxaban highlights its importance in the pharmaceutical industry and its contribution to the development of life-saving medications.

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

• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 
• 446292-07-5 2-((2S)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione 
• 122-98-5 2-Anilinoethanol 
• 446292-04-2 4-(4-nitrophenyl)-3-morpholinone 
• 29518-11-4 4-phenylmorpholin-3-one 
• 1252018-28-2 4-{4-[(5R)-5-(chloromethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one 
• 1074-82-4 potassium phtalimide 
• 1252018-10-2 4-[4-(N-(3-chloro-(2R)-2-hydroxy-1-propyl)amino)phenyl]morpholin-3-one 
• 136918-14-4 phthalimide 
• 1429334-03-1 (S)-1-phthalimido-2-((phenyloxycarbonyl)oxy)-3-propylchloride 
• 148857-42-5 2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione 
• 1313613-18-1 [4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester 
• 1117893-60-3 4-{4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one 
• 556801-12-8 C₂₂H₂₁N₃O₅ 

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 
• 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 
• 1415566-28-7 N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide 
• 446292-10-0 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one 
• 898543-06-1 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholin-3-one hydrochloride 
• 366789-02-8 Rivaroxaban 

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.

Intermediate for synthesizing rivaroxaban, synthesizing method and application

The invention discloses an intermediate for synthesizing rivaroxaban, a synthesizing method and application. The synthesizing method comprises the following steps: firstly, carrying out addition reaction on a structure of formula II and a structure of formula III to obtain a corresponding amino alcohol compound, and then carrying out cyclization reaction on the amino alcohol compound and a carbonylation reagent to obtain a compound of the structure of formula I; carrying out oxidation reaction on the compound of the structure of formula I and an oxidizing agent to obtain a compound of a structure of known formula IV; secondly, desorbing phthaloyl from the compound of the structure of formula IV according to a known method to obtain a compound of a structure of known formula V; and finally,carrying out acylation reaction on the compound of the structure of formula V to obtain the rivaroxaban (a structure of formula VI). The solvent used in the addition reaction is isopropanol or ethanol, and the addition reaction is carried out at a room temperature or under a heating condition. The intermediate for synthesizing the rivaroxaban, the synthesizing method and the application are designed. The intermediate for synthesizing the rivaroxaban has the advantages of cheap and easily obtained raw materials, gentle and easily operated reaction conditions, environmental protection and lesspollution, high yield and purity, easiness in industrialization and the like.