480452-36-6

Basic information

• Product Name: EthanediaMide iMpurity D
• Synonyms: EthanediaMide iMpurity D;tert-Butyl(1R,2S,5S)-2-({2-[(5-chloropyridin-2-yl)aMino]-2-oxoacetyl}aMino)-5-[(diMethylaMino)carbonyl]cyclohexyl-carbaMate;N1-(5-chloropyridin-2-yl)-N2-((1S,2R,4S)-2-[(tert-Butoxycarbonyl)Amino ]-4-[(dimethylamino)carbonyl]-cyclohexyl) oxalamide;Edoxaban Impurity 6;Edoxaban impurity D
• CAS NO: 480452-36-6
• Molecular Formula: C₂₁H₃₀ClN₅O₅
• Molecular Weight: 88.06536
• Mol File: 480452-36-6.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• PKA: 9.46±0.70(Predicted)
• CAS DataBase Reference: EthanediaMide iMpurity D(CAS DataBase Reference)
• NIST Chemistry Reference: EthanediaMide iMpurity D(480452-36-6)
• EPA Substance Registry System: EthanediaMide iMpurity D(480452-36-6)

Safety Data

• Hazardous Substances Data: 480452-36-6(Hazardous Substances Data)

Usage

Description

EthanediaMide iMpurity D, also known as (1R, 2S, 5S)-tert-Buty Edoxaban, is an impurity found in Edoxaban (E555520). Edoxaban is an anticoagulant drug that acts as a direct factor Xa inhibitor, playing a crucial role in the prevention and treatment of various blood clot-related conditions.

Uses

Used in Pharmaceutical Industry:
EthanediaMide iMpurity D is used as an impurity in the development and manufacturing process of Edoxaban for its role in blood clot prevention and treatment. The presence of this impurity is essential for the proper functioning and effectiveness of the drug, as it contributes to the overall anticoagulant properties of Edoxaban.
As an anticoagulant agent, Edoxaban is used for the prevention and treatment of various blood clot-related conditions, such as deep vein thrombosis, pulmonary embolism, and stroke. The presence of EthanediaMide iMpurity D in Edoxaban enhances its ability to inhibit factor Xa, a key enzyme in the coagulation cascade, thus reducing the risk of blood clot formation and associated complications.

Upstream product

• 123536-66-3 (1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 365998-36-3 (1S,2R,4S)-N₂-(tert-butoxycarbonyl)-4-(N,N-dimethylcarbamoyl)-1,2-cyclohexanediamine 
• 349125-08-2 ethyl 2-((5-chloropyridin -2-yl)amino)-2-oxoacetate 
• 365997-33-7 ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate 
• 929693-34-5 ethyl (1S,3R,4R)-3-amino-4-hydroxycyclohexanecarboxylate 
• 365997-31-5 (1S,3S,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid ethyl ester 
• 365997-34-8 ethyl (1S,3R,4S)-4-azido-3-(tert-butoxycarbonylamino)-cyclohexane-1-carboxylate 
• 365997-36-0 (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]cyclohexanecarboxylic acid ethyl ester 
• 552850-73-4 2-((5-chloropyridin-2-yl)amino)-2-oxoacetic acid 
• 67976-82-3 (1S)-3-cyclohexene-1-carboxylic acid (R)-(+)-α-methylbenzylamine salt 

Downstream Products

• 480449-70-5 edoxaban 
• 480449-71-6 [14C]-Edoxaban tosylate 
• 480452-37-7 N¹-[(1S,2R,4S)-2-amino-4-[(dimethylamino)carbonyl]cyclohexyl]-N²-(5-chloro-2-pyridyl)ethanediamide 

Relevant articles and documents

Preparation method of edoxaban tosylate and isomers thereof

The invention discloses a preparation method of edoxaban tosylate and isomers thereof. By taking a compound (I) and a compound (II) as starting materials, the method can be used to prepare any one ofhigh-purity edoxaban tosylate (1S, 2R, 4S), edoxaban tosylate enantiomers (1R, 2S, 4R), edoxaban tosylate epimers (1R, 2R, 4S) and edoxaban tosylate epimers (1S, 2S, 4R). Effective guarantee is provided for process research and quality control of the edoxaban tosylate bulk drug and related preparations, the preparation method is suitable for commercialization, the produced edoxaban tosylate bulk drug is high in purity and has great significance and practical value, and the production of the edoxaban tosylate bulk drug and the control of drug quality are facilitated.

PROCESS FOR PREPARATION OF EDOXABAN

The present invention relates to process for preparation N1-(5-Chloropyridin-2-yl)-N2-[(1S,2R,4S)-4-(N,N-dimethylcarbamoyl)-2-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-ylcarboxamido)cyclohexyl]oxamide p-toluene sulfonate monohydrate [edoxaban tosylate monohydrate], the compound of formula (I), comprising reacting compound of formula (VI) with compound of formula (V) to obtain the compound of formula (IV) and further converting it to edoxaban tosylate monohydrate in an industrially feasible process.

Method for preparing edoxaban from trichloroacetophenone onium salt derivatives

The invention provides a method for preparing edoxaban by using 2, 2, 2-trichloro-1-(4, 5, 6, 7-tetrahydro-5-methylthiazolo[5, 4-c]pyridinium-1-yl) ethanone chloride. The preparation method comprisesthe following steps: preparing 2, 2, 2-trichloro-1-(4, 5, 6, 7-tetrahydro-5-methylthiazolo[5, 4-c]pyridinium-1-yl) ethanone chloride, namely 109C5-11; the invention discloses a preparation method of N1[(1S, 2R, 4S)-2-amino-4-[(dimethylamino) carbonyl]cyclohexyl]-N2(5-chloro-2-pyridyl) oxalamide dimesylate, namely 109T2-31. The 109C5-11 is used as an acylation reagent to prepare the edoxaban with 109T2-31. The preparation method comprises the following steps: preparing the edoxaban by using the 109C5-11 as the acylation reagent; the novel method overcomes the defect that expensive condensing agents EDCI.HCl and activating agents HOBt need to be used in the prior art. The new method provided by the invention is beneficial to more economically and more efficiently realizing industrial scale production of the Edoxaban p-toluenesulfonate hydrate.