Betrixaban maleate

Base Information

• Chemical Name: Betrixaban maleate
• CAS No.: 936539-80-9
• Molecular Formula: C23H22ClN5O3.C4H4O4
• Molecular Weight: 567.986
• European Community (EC) Number: 813-748-5
• Mol file: 936539-80-9.mol

Synonyms:betrixaban maleate;936539-80-9;Betrixaban (maleate);Betrixaban maleate [WHO-DD];N-(5-chloropyridin-2-yl)-2-(4-(N,N-dimethylcarbamimidoyl)benzamido)-5-methoxybenzamide maleate;28Z3021TMU;(Z)-but-2-enedioic acid;N-(5-chloropyridin-2-yl)-2-[[4-(N,N-dimethylcarbamimidoyl)benzoyl]amino]-5-methoxybenzamide;Benzamide, N-(5-chloro-2-pyridinyl)-2-((4-((dimethylamino)iminomethyl)benzoyl)amino)-5-methoxy-, (2Z)-2-butenedioate (1:1);N-(5-Chloro-2-pyridinyl)-2-[[4-[(dimethylamino)iminomethyl]benzoyl]amino]-5-methoxybenzamide (2Z)-2-butenedioate (1;betrixabanmaleate;UNII-28Z3021TMU;BETRIXABAN MALEATE [MI];SCHEMBL20587587;HY-10268A;s5389;AKOS037515630;CCG-270080;AC-35182;BS-52375;CS-0022563;E84423;betrixaban maleate salt;Betrixaban monomaleate

Chemical Property of Betrixaban maleate

Chemical Property:

• PSA: 182.01000
• LogP: 4.09270
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 567.1520759
• Heavy Atom Count: 40
• Complexity: 787

Purity/Quality:

98%,99%, ^*data from raw suppliers

Betrixabanmaleate >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=N)C1=CC=C(C=C1)C(=O)NC2=C(C=C(C=C2)OC)C(=O)NC3=NC=C(C=C3)Cl.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: CN(C)C(=N)C1=CC=C(C=C1)C(=O)NC2=C(C=C(C=C2)OC)C(=O)NC3=NC=C(C=C3)Cl.C(=C\C(=O)O)\C(=O)O
• Recent EU Clinical Trials: Multicenter, Randomized, Active-Controlled Efficacy And Safety Study Comparing Extended Duration Betrixaban With Standard Of Care Enoxaparin For The Prevention Of Venous Thromboembolism In Acute Medically Ill Patients

Technology Process of Betrixaban maleate

There total 5 articles about Betrixaban maleate 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: 88.8%

betrixaban (330942-05-7) + maleic acid (110-16-7,26099-09-2) → N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylcarbamimidoyl)benzamido]-5-methoxybenzamide maleic acid salt (936539-80-9)

Guidance literature:

In ethanol; water; at 55 ℃; for 1h;

Reference yield: 85.4%

N-(5-chloro(2-pyridyl)){2-[(4-cyanophenyl)carbonylamino]-5-methoxyphenyl}carboxamide (330942-01-3) + dimethylaminomagnesium chloride + maleic acid (110-16-7,26099-09-2) → N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylcarbamimidoyl)benzamido]-5-methoxybenzamide maleic acid salt (936539-80-9)

Guidance literature:

N-(5-chloro(2-pyridyl)){2-[(4-cyanophenyl)carbonylamino]-5-methoxyphenyl}carboxamide; dimethylaminomagnesium chloride; In tetrahydrofuran; at 0 - 15 ℃;

maleic acid; In tetrahydrofuran; water; at 10 - 15 ℃;

Reference yield:

2-amino-N-(5-chloro-pyridin-2-yl)-5-methoxy-benzamide (280773-17-3) → N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylcarbamimidoyl)benzamido]-5-methoxybenzamide maleic acid salt (936539-80-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 1.5 h / 30 °C

2: acetyl chloride; zinc(II) chloride / methanol / 9.5 h / -5 - 25 °C

3: ethanol; water / 1 h / 55 °C

With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; acetyl chloride; zinc(II) chloride; In tetrahydrofuran; methanol; ethanol; water;

upstream raw materials:

betrixaban

maleic acid

4-cyanobenzoic Acid

2-amino-N-(5-chloro-pyridin-2-yl)-5-methoxy-benzamide

Refernces

• 1、 -. "Synthetic process of betrixaban". Paragraph 0018; 0022-0023; 0027-0028; 0032. . Retrieved 2019/11/12.
• 2、 -. "Preparation method of betrixaban maleate". Paragraph 0037-0038; 0044-0045; 0051-0052. . Retrieved 2018/03/24.