EthanediaMide iMpurity D

Base Information

• Chemical Name: EthanediaMide iMpurity D
• CAS No.: 480452-36-6
• Molecular Formula: C21H30ClN5O5
• Molecular Weight: 467.953
• Mol file: 480452-36-6.mol

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

Chemical Property of EthanediaMide iMpurity D

Chemical Property:

• PKA: 9.46±0.70(Predicted)
• PSA: 129.73000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 2.79470

Purity/Quality:

99%+ ^*data from raw suppliers

Edoxabanimpurity4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of EthanediaMide iMpurity D

There total 45 articles about EthanediaMide iMpurity D which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

[(5-chloropyridin-2-yl)amino]-2-glyoxylic acid ethyl ester monohydrochloride + (1R,2S,5S)-1-amino-4-(dimethylaminocarbonyl)-cyclohexyl-2-carbamic acid tert-butyl ester oxalate → carbamic acid, N-[(1R,2S,5S)-2-[[2-[(5-chloro-2-pyridinyl)amino]-2-oxoacetyl]amino]-5-[(dimethylamino)carbonyl]cyclohexyl]-1,1-dimethylethyl ester (480452-36-6)

Guidance literature:

With 1-butyl-3-methylimidazolium hydroxide; pyridine; triethylamine; In acetonitrile; at 45 - 60 ℃; for 4h; Reagent/catalyst;

Reference yield: 92.2%

(1S,2R,4S)-N2-(tert-butoxycarbonyl)-4-(N,N-dimethylcarbamoyl)-1,2-cyclohexanediamine (365998-36-3) + ethyl 2-((5-chloropyridin -2-yl)amino)-2-oxoacetate (349125-08-2) → carbamic acid, N-[(1R,2S,5S)-2-[[2-[(5-chloro-2-pyridinyl)amino]-2-oxoacetyl]amino]-5-[(dimethylamino)carbonyl]cyclohexyl]-1,1-dimethylethyl ester (480452-36-6)

Guidance literature:

With triethylamine; In acetonitrile; at 50 - 60 ℃; for 8h; Time; Large scale;

Reference yield: 91.05%

(1R,2S,5S)-1-amino-4-(dimethylaminocarbonyl)-cyclohexyl-2-carbamic acid tert-butyl ester oxalate + 2-((5-chloropyridin-2-yl)amino)-2-oxoacetic acid (552850-73-4) → carbamic acid, N-[(1R,2S,5S)-2-[[2-[(5-chloro-2-pyridinyl)amino]-2-oxoacetyl]amino]-5-[(dimethylamino)carbonyl]cyclohexyl]-1,1-dimethylethyl ester (480452-36-6)

Guidance literature:

With dibutyltin(II) dilaurate; sodium hydrogencarbonate; at 50 - 70 ℃; for 5h; pH=7; Temperature; Reagent/catalyst; Autoclave; Industrial scale;

upstream raw materials:

tert-butyl N-[(1R,2S,5S)-2-azido-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate

5-chloro-2-pyridylamine

(1S,3S,6R)-N,N-dimethyl-7-oxabicyclo[4.1.0]heptane-3-carboxamide

(1S,3R,4R)-3-amino-4-hydroxy-N,N-dimethyl cyclohexanecarboxamide

Downstream raw materials:

edoxaban

[14C]-Edoxaban tosylate

N¹-[(1S,2R,4S)-2-amino-4-[(dimethylamino)carbonyl]cyclohexyl]-N²-(5-chloro-2-pyridyl)ethanediamide

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF EDOXABAN". Page/Page column 12; 20-22. . Retrieved 2021/01/23.
• 2、 -. "Improved preparation method of edoxaban intermediate". Paragraph 0023-0064. . Retrieved 2020/10/21.