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

Uses

(1R, 2S, 5S)-tert-Buty Edoxaban is an impurity of Edoxaban (E555520). Edoxaban is an anticoagulant drug which acts as a direct factor Xa inhibitor.

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.

Improved preparation method of edoxaban intermediate

The invention belongs to the field of organic synthesis, and particularly relates to an improved preparation method of an edoxaban intermediate. In most preparation methods for preparing the compound(1), a system is extremely easy to be in a cured state in the reaction process, the system is difficult to stir, and finally, the problems of product yield reduction, quality deterioration and the like are caused. In order to solve the problem of curing in the system, the improved preparation method of an edoxaban intermediate is expected to be provided. In the process of synthesizing the compound(1), alcohol or a mixture of alcohol and acetonitrile is used as a reaction solvent, so that the reaction system is in a clear state at the beginning, the product is gradually separated out along with the reaction, the product is uniformly dispersed in the solvent in the whole process from the beginning to the end of the reaction and is easy to stir, and the curing problem in the reaction processis effectively solved.