Rilpivirine Hydrochloride

Base Information

• Chemical Name: Rilpivirine Hydrochloride
• CAS No.: 700361-47-3
• Molecular Formula: C22H18N6.ClH
• Molecular Weight: 402.886
• European Community (EC) Number: 680-634-8
• UNII: 212WAX8KDD
• ChEMBL ID: CHEMBL1628504
• DSSTox Substance ID: DTXSID80220320
• NCI Thesaurus Code: C152217
• RXCUI: 1102287
• Wikidata: Q27137040
• Mol file: 700361-47-3.mol

Synonyms:278, TMC;HCl, Rilpivirine;Hydrochloride, Rilpivirine;R278474;Rilpivirine;Rilpivirine HCl;Rilpivirine Hydrochloride;TMC 278;TMC-278;TMC278

Chemical Property of Rilpivirine Hydrochloride

Chemical Property:

• PSA: 100.65000
• LogP: 5.28596
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 402.1359723
• Heavy Atom Count: 29
• Complexity: 607

Purity/Quality:

99.3% ^*data from raw suppliers

RILPIVIRINE HYDROCHLORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)C=CC#N.Cl
• Isomeric SMILES: CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)/C=C/C#N.Cl
• Recent ClinicalTrials: A Study of Bioavailability and Food Effect of SACT-1 and Edurant? Tablets in Healthy Adult Volunteers
• Recent EU Clinical Trials: HIV-1 RNA suppression and drug concentrations in semen, cervicovaginal fluid and rectum in HIV-1 infected individuals receiving intramuscular long-acting cabotegravir plus rilpivirine (“CAR-GR Study)
• Uses: Rilpivirine Hydrochloride was shown to be able to treat and or prevent immunodeficiency virus-1. It also has uses for anti-viral therapy
• Clinical Use: Rilpivirine hydrochloride (Edurant), a non-nucleoside reverse transcriptase inhibitor (NNRTI), received its approval both from the U.S. FDA and E.U. EMA in 2011 for the treatment of HIV-1 infection in treatment-na?ve adult patients. It was discovered and developed by Janssen Pharmaceuticals and its subsidiary Tibotec Pharmaceuticals. As a second generation NNRTI, rilpivirine hydrochloride displayed higher potency and longer half-life with a 25 mg once a day dose, compared to existing NNRTIs, such as the 200 mg BID of efavirenze (Sustiva). In late 2011, the fixed-dose combination products of rilpivirine hydrochloride with two nucleoside reverse transcriptase inhibitor (RTIs) emtricitabine and tenofovir disoproxil fumarate, co-developed by Gilead Science and Tibotec, were also approved both by the FDA and EMA under brand names Complera? and Eviplera?, respectively.

Technology Process of Rilpivirine Hydrochloride

There total 24 articles about Rilpivirine Hydrochloride 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: 90.0%

rilpivirine (500287-72-9) → Rilpivirine hydrochloride (700361-47-3)

Guidance literature:

With hydrogenchloride; acetic acid; In water; at 90 - 95 ℃;

Reference yield: 83.0%

tert-butyl (2-chloropyrimidin-4-yl){4-[(E)-2-cyanoethenyl]-2,6-dimethylphenyl}carbamate + 4-Aminobenzonitrile (873-74-5) → Rilpivirine hydrochloride (700361-47-3)

Guidance literature:

With hydrogenchloride; acetic acid; In water; for 1h; Inert atmosphere; Reflux;

Reference yield: 80.0%

methyl (E)-(2-((4-cyanophenyl)amino)pyrimidin-4-yl)(4-(2-cyanoethenyl)-2,6-dimethylphenyl)carbamate → Rilpivirine hydrochloride (700361-47-3)

Guidance literature:

methyl (E)-(2-((4-cyanophenyl)amino)pyrimidin-4-yl)(4-(2-cyanoethenyl)-2,6-dimethylphenyl)carbamate; With acetic acid; lithium chloride; at 150 ℃; for 1h; Microwave irradiation;

With hydrogenchloride; In water; isopropyl alcohol;

upstream raw materials:

rilpivirine

4-Aminobenzonitrile

4-[(4-hydroxy-2-pyrimidinyl)amino]benzonitrile

(2E)-3-(4-amino-3,5-dimethylphenyl)prop-2-enenitrile hydrochloride

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF RILPIVIRINE". Page/Page column 17; 20-21. . Retrieved 2020/06/10.
• 2、 -. "RILPIVIRINE HYDROCHLORIDE". Page/Page column 10; 11. . Retrieved 2013/03/28.