Vipadenant

Base Information

• Chemical Name: Vipadenant
• CAS No.: 442908-10-3
• Molecular Formula: C16H15N7O
• Molecular Weight: 321.341
• Mol file: 442908-10-3.mol

Synonyms:CEB-4520;VER-ADO-49;V-2006;VER-A00-11;Vipadenant;UNII-LDR3USH1NJ;

Chemical Property of Vipadenant

Chemical Property:

• PSA: 122.40000
• LogP: 2.51370

Purity/Quality:

99% ^*data from raw suppliers

Vipadenant ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Vipadenant (also known as BIIB014) is a potent, selective oral adenosine A2A receptor antagonist under development for the treatment of Parkinson’s disease. It has successfully completed phase I clinical studies. It might also be a potential adjunctive therapy reagent for cancer treatment. It was found that it has certain potentials to disrupt an immunosuppressive mechanism of tumour protection, generating improved efficacy for immunotherapies of certain cancers when used in combination with other drugs.
• Uses: Vipadenant is a potent, selective and orally available adenosine A2A receptor antagonist under development for for Parkinson''s disease. Vipadenant demonstrates strong oral activity in commonly used models of Parkinson''s disease. Vipadenant has shown excellent preclinical pharmacokinetics and has successfully completed phase I clinical studies.

Technology Process of Vipadenant

There total 5 articles about Vipadenant 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: 92.0%

7-(furan-2-yl)-3-(3-methyl-4-nitrobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine (442908-07-8) → Vipadenant (442908-10-3)

Guidance literature:

With formic acid; triethylamine; 5% palladium over charcoal; In tetrahydrofuran; at 70 ℃; for 5h;

Reference yield:

7-(2-furyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (442906-78-7) + 4-(bromomethyl)-2-methyl-1-nitrobenzene (141281-38-1) → Vipadenant (442908-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C

1.2: 1 h / 20 °C

2.1: hydrogenchloride; tin(ll) chloride / ethanol / 2 h / 50 °C

With hydrogenchloride; sodium hydride; tin(ll) chloride; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm800961g

Reference yield:

3-(4-amino-3-methylbenzyl)-7-(furan-2-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine tetrahydrofurane hemisolvate → Vipadenant (442908-10-3)

Guidance literature:

at 20 - 170 ℃; Product distribution / selectivity;

upstream raw materials:

7-(furan-2-yl)-3-(3-methyl-4-nitrobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine

7-(2-furyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine

4-(bromomethyl)-2-methyl-1-nitrobenzene

Refernces

• 1、 -. "POLYMORPHS AND SOLVATES OF A PHARMACEUTICAL AND METHODS OF MAKING". Page/Page column 22. . Retrieved 2008/12/07.