Darexaban

Base Information

• Chemical Name: Darexaban
• CAS No.: 365462-23-3
• Molecular Formula: C27H30N4O4
• Molecular Weight: 474.55200
• UNII: KF322K101S
• DSSTox Substance ID: DTXSID101030146
• Nikkaji Number: J2.437.544G
• Wikipedia: Darexaban
• Wikidata: Q5222570
• NCI Thesaurus Code: C90973
• Pharos Ligand ID: 4LPY8SZCJGC4
• Metabolomics Workbench ID: 153305
• ChEMBL ID: CHEMBL1922235
• Mol file: 365462-23-3.mol

Synonyms:darexaban;N-(2-hydroxy-6-(4-methoxybenzamido)phenyl)-4-(4-methyl-1,4-diazepan-1-yl)benzamide;YM 150;YM-150;YM150 cpd

Chemical Property of Darexaban

Chemical Property:

• PSA: 94.14000
• LogP: 4.19620
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 474.22670545
• Heavy Atom Count: 35
• Complexity: 691

Purity/Quality:

99% ^*data from raw suppliers

Darexaban ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCCN(CC1)C2=CC=C(C=C2)C(=O)NC3=C(C=CC=C3O)NC(=O)C4=CC=C(C=C4)OC
• Recent ClinicalTrials: A Study Evaluating Efficacy and Safety of YM150 Compared to Enoxaparin in Subjects Undergoing Hip Replacement Surgery
• Recent EU Clinical Trials: A Randomized, Double-Blind, Placebo Controlled Multi-Center and Parallel Group Study of the Safety, Tolerability and Efficacy of YM150 in combination with Standard Treatment in Secondary Prevention of Ischemic Vascular Events in Subjects with Acute Coronary Syndromes.

Technology Process of Darexaban

There total 4 articles about Darexaban 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:

N-(2-hydroxy-6-nitrophenyl)-4-(4-methyl-1,4-diazepan-1-yl)benzamide (365462-76-6) → Darexaban (365462-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 30 °C / 760.05 Torr

2: pyridine / 72 h / 20 °C

With pyridine; palladium 10% on activated carbon; hydrogen; In methanol;

DOI:10.1021/jm200868m

Reference yield:

2-amino-3-nitrophenyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate hydrochloride (365462-75-5) → Darexaban (365462-23-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / acetonitrile / 6 h / 70 °C

1.2: 14 h / 20 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol / 30 °C / 760.05 Torr

3.1: pyridine / 72 h / 20 °C

With pyridine; palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; acetonitrile;

DOI:10.1021/jm200868m

Reference yield:

2-Amino-3-nitrophenol (603-85-0) → Darexaban (365462-23-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / acetonitrile / 21 h / 5 °C

2.1: triethylamine / acetonitrile / 6 h / 70 °C

2.2: 14 h / 20 °C

3.1: palladium 10% on activated carbon; hydrogen / methanol / 30 °C / 760.05 Torr

4.1: pyridine / 72 h / 20 °C

With pyridine; palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; acetonitrile;

DOI:10.1021/jm200868m

upstream raw materials:

N-(2-hydroxy-6-nitrophenyl)-4-(4-methyl-1,4-diazepan-1-yl)benzamide

2-amino-3-nitrophenyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate hydrochloride

N-(2-amino-6-hydroxyphenyl)-4-(4-methyl-1,4-diazepan-1-yl)benzamide

4-methoxy-benzoyl chloride

Downstream raw materials:

C₂₉H₃₄N₄O₅

Darexaban hydrochloride

ethyl (3-[(4-methoxybenzoyl)amino]-2-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}phenoxy)acetate hydrochloride

(3-[(4-methoxybenzoyl)amino]-2-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}phenoxy)acetic acid hydrochloride

Refernces