Edoxaban

Base Information

• Chemical Name: Edoxaban
• CAS No.: 912273-65-5
• Molecular Formula: C₇H₈O₃S*C₂₄H₃₀ClN₇O₄S
• Molecular Weight: 720.27
• Mol file: 912273-65-5.mol

Synonyms:N-(5-Chloro-2-pyridinyl)-N'-[(1S,2R,4S)-4-[(dimethylamino)carbonyl]-2-[[(4,5,6,7-tetrahydro-5-methylthiazolo[5,4-c]pyridin-2-yl)carbonyl]amino]cyclohexyl]ethanediamide; DU 176b

Chemical Property of Edoxaban

Chemical Property:

• PSA: 164.87000
• Density: 1.43
• LogP: 2.08230

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Edoxaban

There total 109 articles about Edoxaban 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: 86.0%

edoxaban (480449-70-5) + toluene-4-sulfonic acid (104-15-4) → N1-(5-chloropyridin-2-yl)-N2-((1S,2R,4S)-4-[(dimethylamino)carbonyl]-2-{[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]amino}cyclohexyl)ethanediamide p-toluenesulfonate (912273-65-5)

Guidance literature:

In ethanol; water; at 20 - 60 ℃; for 24h;

Reference yield:

(1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-N,N-dimethylcyclohexanecarboxamide (929693-30-1) → [14C]-Edoxaban tosylate (480449-71-6,912273-65-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / 4-methyl-2-pentanone (MIBK) / 1 h / 20 °C

2.1: sodium azide; N-dodecylpyridinium chloride / toluene; water / 47 h / 60 - 63 °C / Dean-Stark

3.1: ammonium formate / palladium-carbon / methanol / 1 h / 40 °C

3.2: 17 h / 20 °C

4.1: triethylamine / acetonitrile / 6 h / 60 °C

5.1: methanesulfonic acid / acetonitrile / 2 h / 20 °C

5.2: 16 h / 20 °C / Cooling with ice

6.1: dichloromethane; ethanol

With sodium azide; methanesulfonic acid; ammonium formate; N-dodecylpyridinium chloride; triethylamine; palladium-carbon; In methanol; ethanol; dichloromethane; 4-methyl-2-pentanone (MIBK); water; toluene; acetonitrile;

Reference yield:

2-[(5-chloro-2-pyridyl)amino]-2-oxoacetic acid allyl ester hydrochloride + N-[(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]-4,5,6,7-tetrahydro-5-methylthiazolo[5 ,4-c]pyridin-2-carboxamide dihydrochloride + toluene-4-sulfonic acid (104-15-4) → [14C]-Edoxaban tosylate (480449-71-6,912273-65-5)

Guidance literature:

2-[(5-chloro-2-pyridyl)amino]-2-oxoacetic acid allyl ester hydrochloride; N-[(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]-4,5,6,7-tetrahydro-5-methylthiazolo[5 ,4-c]pyridin-2-carboxamide dihydrochloride; With triethylamine; In acetonitrile; at 40 - 75 ℃;

toluene-4-sulfonic acid; In ethanol; water; at 75 - 80 ℃;

upstream raw materials:

edoxaban

toluene-4-sulfonic acid

carbamic acid, N-[(1R,2S,5S)-2-[[2-[(5-chloro-2-pyridinyl)amino]-2-oxoacetyl]amino]-5-[(dimethylamino)carbonyl]cyclohexyl]-1,1-dimethylethyl ester

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