6-Desamino 6-Chloro Etravirine

Base Information

• Chemical Name: 6-Desamino 6-Chloro Etravirine
• CAS No.: 269055-76-7
• Molecular Formula: C20H13BrClN5O
• Molecular Weight: 454.713
• DSSTox Substance ID: DTXSID80471895
• Wikidata: Q72452528
• Mol file: 269055-76-7.mol

Synonyms:6-Desamino 6-Chloro Etravirine;269055-76-7;4-[[5-Bromo-6-chloro-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethylbenzonitrile;4-[5-bromo-6-chloro-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile;4-((5-Bromo-6-chloro-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethylbenzonitrile;4-[[5-Bromo-6-chloro-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-benzonitrile;SCHEMBL247490;DTXSID80471895;ODWHQRYHASBLKO-UHFFFAOYSA-N;4-[[5-Bromo-6-chloro-2-[(4-cyanophenyl)amino]-4-pyrimidinyl] oxy]-3,5-dimethyl-benzonitrile;FT-0665913;4-[[5-bromo-4-(4-cyano-2,6-dimethylpbenoxy)-6-chloro-2-pyrimidinyl]amino]-benzonitrile;4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidiny]amino]-benzonitrile;4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]-benzonitrile;4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]benzonitrile;4-[[5-bromo4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]-benzonitrile;4-[[5-bromo4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]benzonitrile;4-[5-bromo-6-chloro-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3, 5-dimethylbenzonitrile

Chemical Property of 6-Desamino 6-Chloro Etravirine

Chemical Property:

• Boiling Point: 626.1±65.0 °C(Predicted)
• PKA: -2.23±0.10(Predicted)
• PSA: 94.62000
• Density: 1.60
• LogP: 5.86156
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 452.99920
• Heavy Atom Count: 28
• Complexity: 613

Purity/Quality:

98%min ^*data from raw suppliers

6-Desamino6-ChloroEtravirine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1OC2=C(C(=NC(=N2)NC3=CC=C(C=C3)C#N)Cl)Br)C)C#N
• Uses: An intermediate in the production of Etravirine

Technology Process of 6-Desamino 6-Chloro Etravirine

There total 5 articles about 6-Desamino 6-Chloro Etravirine 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: 45.0%

3,5-dimethyl-4-hydroxybenzonitrile (4198-90-7) + 4-[[(5-bromo-4,6-dichloro)-2-pyrimidinyl]amino]benzonitrile (269055-75-6) → 4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]-benzonitrile (269055-76-7)

Guidance literature:

3,5-dimethyl-4-hydroxybenzonitrile; With sodium hydride; In 1,4-dioxane; for 0.0333333h;

With 1-methyl-pyrrolidin-2-one; In 1,4-dioxane; for 0.166667h;

4-[[(5-bromo-4,6-dichloro)-2-pyrimidinyl]amino]benzonitrile; In 1,4-dioxane; at 155 ℃; for 16h;

Reference yield: 45.0%

4-[[(5-bromo-4,6-dichloro)-2-pyrimidinyl]amino]benzonitrile (269055-75-6) + sodium 4-cyano-2,6-dimethylphenolate → 4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]-benzonitrile (269055-76-7)

Guidance literature:

With 1-Methylpyrrolidine; In 1,4-dioxane;

DOI:10.1016/S0960-894X(01)00412-7

Reference yield:

4-(4,6-dichloropyrimidine-2-yl-amino)benzonitrile (329187-59-9) → 4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]-benzonitrile (269055-76-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Br₂; NaHCO₃ / H₂O; methanol

2: 45 percent / N-methylpyrrolidine / dioxane

With 1-Methylpyrrolidine; bromine; sodium hydrogencarbonate; In 1,4-dioxane; methanol; water;

DOI:10.1016/S0960-894X(01)00412-7

upstream raw materials:

4-[[(5-bromo-4,6-dichloro)-2-pyrimidinyl]amino]benzonitrile

4-(4,6-dichloropyrimidine-2-yl-amino)benzonitrile

4-((4,6-dihydroxypyrimidine-2-yl)amino)benzonitrile

4-cyanophenyl guanidine hydrochloride

Downstream raw materials:

4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-(methoxyamino)-2-pyrimidinyl]amino]-benzonitrile

etravirine

Refernces

• 1、 Ludovici, Donald W.,De Corte, Bart L.,Kukla, Michael J.,Ye, Hong,Ho, Chih Y.,Lichtenstein, Mark A.,Kavash, Robert W.,Andries, Koen,De Bethune, Marie-Pierre,Azijn, Hilde,Pauwels, Rudi,Lewi, Paul J.,Heeres, Jan,Koymans, Lucien M.H.,De Jonge, Marc R.,Van Aken, Koen J.A.,Daeyaert, Frederik F.D.,Das, Kalyan,Arnold, Edward,Janssen, Paul A.J.. "Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues". . p. 2235 - 2239. Retrieved 2007/10/03.