Edoxaban (TsOH salt)

Base Information

• Chemical Name: Edoxaban (TsOH salt)
• CAS No.: 480449-71-6
• Molecular Formula: C24H30ClN7O4S.C7H7HSO3
• Molecular Weight: 720.27
• Mol file: 480449-71-6.mol

Synonyms:Edoxaban Tosylate

Chemical Property of Edoxaban (TsOH salt)

Chemical Property:

• PSA: 227.62000
• LogP: 4.40480

Purity/Quality:

99.5% ^*data from raw suppliers

Edoxaban >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Edoxaban (TsOH salt)

There total 74 articles about Edoxaban (TsOH salt) 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:

(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 ℃;

Reference yield:

5-methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloric acid salt (720720-96-7) + ethanediamide, N1-[(1S,2R,4S)-2-amino-4-[(dimethylamino)carbonyl]cyclohexyl]-N2-(5-chloro-2-pyridinyl)-, dihydrochloride + toluene-4-sulfonic acid (104-15-4) → [14C]-Edoxaban tosylate (480449-71-6,912273-65-5)

Guidance literature:

5-methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloric acid salt; ethanediamide, N¹-[(1S,2R,4S)-2-amino-4-[(dimethylamino)carbonyl]cyclohexyl]-N²-(5-chloro-2-pyridinyl)-, dihydrochloride; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; at 0 - 0.3 ℃; for 0.18h;

toluene-4-sulfonic acid; In water; dimethyl sulfoxide; at 0.25 - 0.7 ℃; for 0.01h; Solvent; Temperature;

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

Refernces

• 1、 -. "Preparation method of edoxaban tosylate and isomers thereof". . . Retrieved 2021/02/06.
• 2、 -. "Method for preparing edoxaban from trichloroacetophenone onium salt derivatives". . . Retrieved 2020/07/21.