1313613-18-1

Basic information

• Product Name: N-[4-(3-oxo-4-morpholinyl)phenyl]carbamic acid phenylmethyl ester
• CAS NO: 1313613-18-1
• Molecular Formula: C₁₈H₁₈N₂O₄
• Molecular Weight: 326.35192
• Mol File: 1313613-18-1.mol

Chemical Properties

• CAS DataBase Reference: N-[4-(3-oxo-4-morpholinyl)phenyl]carbamic acid phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-(3-oxo-4-morpholinyl)phenyl]carbamic acid phenylmethyl ester(1313613-18-1)
• EPA Substance Registry System: N-[4-(3-oxo-4-morpholinyl)phenyl]carbamic acid phenylmethyl ester(1313613-18-1)

Safety Data

• Hazardous Substances Data: 1313613-18-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-[4-(3-oxo-4-Morpholinyl)phenyl]carbaMic acid phenylMethyl ester is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the formation of new compounds with potential applications in different fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, N-[4-(3-oxo-4-Morpholinyl)phenyl]carbaMic acid phenylMethyl ester is utilized as a key intermediate in the development of pharmaceutical drugs. Its unique structure and reactivity contribute to the synthesis of novel drug candidates with potential therapeutic benefits.
Used in Medicinal Chemistry:
N-[4-(3-oxo-4-Morpholinyl)phenyl]carbaMic acid phenylMethyl ester is employed in medicinal chemistry for its potential to be incorporated into drug molecules, enhancing their pharmacological properties and improving their efficacy in treating various diseases.
Used in Drug Development:
N-[4-(3-oxo-4-Morpholinyl)phenyl]carbaMic acid phenylMethyl ester plays a significant role in drug development, as its properties and potential uses make it an interesting and important chemical entity for further study and application in the pharmaceutical industry. Its versatility in chemical reactions and ability to be incorporated into drug molecules contribute to the discovery of new therapeutic agents.

Upstream product

• 501-53-1 benzyl chloroformate 
• 2524-67-6 4-morpholino-4-yl-phenylamine 
• 348626-43-7 4-(4-morpholinyl)-N-benzyloxycarbonylaniline 
• 106-40-1 4-bromo-aniline 
• 29518-11-4 4-phenylmorpholin-3-one 
• 446292-04-2 4-(4-nitrophenyl)-3-morpholinone 
• 122-98-5 2-Anilinoethanol 
• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 

Downstream Products

• 1117893-60-3 4-{4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one 
• 366789-02-8 Rivaroxaban 
• 1117893-61-4 R-(2-oxo-3-((4-(3-oxo-morpholinyl)phenyl)oxazolidin-5-yl))methylmethanesulfonate 
• 1313613-19-2 4-(4-((S)-5-(tert-butylaminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one 
• 1313613-22-7 4-(4-((S)-5-(tert-octylaminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one 
• 1313613-21-6 5-chloro-N-tert-butyl-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl}thiophene-2-carboxamide 
• 1313613-23-8 5-chloro-N-tert-octyl-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl}thiophene-2-carboxamide 
• 1313613-20-5 4-(4-((S)-5-(tert-butylaminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one methanesulfonic salt 
• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 
• 1414932-73-2 (S)-4-(4-{5-[(benzylidene-amino)-methyl]-2-oxo-oxazolidine-3-yl}-phenyl)-morpholin-3-one 
• 1450915-99-7 4-{4-[(R)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one 
• 865479-71-6 5-chloro-N-({(5R)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide 
• 1429334-00-8 (S)-N-[{3-(4-(3-oxomorpholin-4-yl)phenyl)-2-oxo-1,3-oxazolidin-5-yl}methyl]acetamide 
• 1372665-04-7 4-{4-[(5S)-5-((dibenzylamino)methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one 

Relevant articles and documents

Preparation method of rivaroxaban intermediate

The invention discloses a preparation method of a Rivaroxaban intermediate. The preparation method includes the following steps that (1) in existence of an organic lithium salt or the organic lithiumsalt and an inorganic lithium salt, a compound in a following formula I is reacted with a compound in a following formula II to obtain a compound in a following formula III; and (2) the compound in the formula III is subjected to an acidification reaction in existence of inorganic acid HX, the Rivaroxaban intermediate shown in a following formula IV is obtained, wherein R in the compound in the formula I is selected from methyl, isopropyl, normal-butyl and phenyl or benzyl, and the inorganic acid HX is selected from hydrochloric acid or sulfuric acid. The preparation method is easy to operateand high in yield, and industrial production and patent medicine quality control are convenient.

Preparation method of Rivaroxaban intermediates

The invention discloses a preparation method of Rivaroxaban intermediates. The invention relates to a green and efficient preparation method of 4-(4-aminophenyl)morpholinyl-3-one and an amino protected derivative thereof. A structure of a formula II is obtained through an oxidation reaction of a structure of a formula II, and a structure of a formula I can be obtained through a deprotection reaction of the structure of the formula II, wherein the compound I and the compound II are both important intermediates for synthesizing the anticoagulation drug Rivaroxaban. Potassium permanganate is usedas an oxidizing agent in the oxidation reaction, tetraethyl benzyl ammonium chloride (TEBAC) is used as a phase transfer catalyst, dichloromethane is used as a solvent, and the reaction temperature in the oxidation reaction is 15-55 DEG C. The invention provides the preparation method of the Rivaroxaban intermediates, and the preparation method has the advantages that the raw materials are cheapand easily available, the reactions are mild in condition and are easy to operate, the preparation method is green and is friendly to the environment, the intermediate products and the final product are easy to purify, the total yield is high, industrial production is easy to realize, and the preparation method is effective and practical.

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.

PROCESS FOR OBTAINING RIVAROXABAN AND INTERMEDIATE THEREOF

This invention relates to a procedure for obtaining a thiophene-2-carboxamide compound, specifically rivaroxaban, which comprises the (i) fragmentation of the N═C bond of a compound of formula 23 where R1 is selected among hydrogen, halogen, and (C1-C6)alkyl; and (ii) acylation of the resulting intermediate with 5-chloro-tiofen-2-carbonyl chloride in a solvent medium, in the presence of a base. The invention also relates to the compounds of formula 23 and their use in the obtention of rivaroxaban.

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

The present invention relates to processes for the preparation of oxazolidinone derivatives. More particularly the present invention provides processes for the preparation of 5-chloro-N-( {(5S)-2-oxo-3-[4-(3-oxo-4-moφholinyl)phenyl]-1,3-oxazolidin-5-yl methyl)-2-thiophene-carboxamide and intennediates thereof. Where L is a leaving group like halogen atom (F, CI, Br, I) or -OS02R where R = C'-4 alkyl straight chain or branched chain, sub or unsubstituted aryl, sub or unsub aryl alkyl; with a suitable reagent to provide the compound of formula (II). The reaction step is performed by reacting the compound of formula (IV) with amine source which may be dissolved in solvent like water or alcohol. For example ammonium hydroxide.

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.

A PROCESS FOR THE PREPARATION OF RIVAROXABAN BASED ON THE USE OF (S)-EPICHLOROHYDRIN

The invention relates to the stereoisomers of 4-{4-[(S/R)-5-[(((aryl)methylene)- amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-ones described by the chemical formulae (S)-(9) and (R)-(9). The optical isomer of compound (9) with the (S)- configuration is industrially applicable for the manufacture of the antithrombotic drug rivaroxaban (1). The new preparation process of rivaroxaban comprises a reaction of (S)-1- chloro-3-(((aryl)methylene)amino)propan-2-ols (S)-(14) with alkyl 4-(3-oxomorpholine-4- yl)phenylcarbamates (15) providing the key intermediate (S)-(9), which is further subjected to hydrolytic deprotection and subsequent acylation, producing rivaroxaban. The commercially available (S)-epichlorohydrin has been conveniently used as the chiral building block for the production of the key intermediate.

PROCESS FOR OBTAINING RIVAROXABAN AND INTERMEDIATE THEREOF

This invention relates to a procedure for obtaining a thiophene-2-carboxamide compound, specifically rivaroxaban, which comprises the (i) fragmentation of the N=C bond of a compound of formula 23 where R1 is selected among hydrogen, halogen, and (C1-C6)alkyl; and (ii) acylation of the resulting intermediate with 5-chloro-tiofen-2-carbonyl chloride in a solvent medium, in the presence of a base. The invention also relates to the compounds of formula 23 and their use in the obtention of rivaroxaban.

PROCESS FOR THE PREPARATION OF RIVAROXABAN AND INTERMEDIATES THEREOF

A process for the preparation of rivaroxaban, or a pharmaceutically acceptable salt thereof, or a solvate thereof, including a hydrate, comprising submitting an amine compound of formula (III) wherein R1 is a (C4-C10)-alkyl radical which is attached to the N atom by a tertiary C atom, first to an acylation reaction and then to a dealkylation reaction.

Method for the preparation of rivaroxaban

The present invention relates to the use of a compound having the formula (II) for the preparation of a compound having the formula (V). Methods of preparing the compound having the formula (V) using the compound having the formula (II) are also described. Individual reaction steps as well as intermediates are additionally claimed.