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Etravirine
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Name

Etravirine

 EINECS 682-331-6
CAS No. 269055-15-4 Density 1.57 g/cm3
PSA N/A LogP N/A
Solubility N/A Melting Point 265oC (dec.)
Formula C20H15BrN6O Boiling Point 637.4 °C at 760 mmHg
Molecular Weight 435.283 Flash Point 339.3 °C
Transport Information N/A Appearance white to off-white solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 269055-15-4 (4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3, 5 –dimethylbenzonitrile) Hazard Symbols N/A
Synonyms

4-(6-Amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile;Intelence;R 165335;TMC 125;Benzonitrile,4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-;

Article Data 20

Etravirine Synthetic route

4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile

269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: 4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile With bromine In propan-1-ol at 5 - 20℃;
Stage #2: With sodium hydroxide In propan-1-ol; water at 0 - 20℃; Product distribution / selectivity;		92.82%
With bromine In dichloromethane at 0 - 5℃; for 4h;80%
With bromine In dichloromethane at 0 - 5℃; for 5h;80.2%
1398507-09-9

4-((4-amino-5-bromo-6-chloropyrimidin-2-yl)amino)benzonitrile

4198-90-7

3,5-dimethyl-4-hydroxybenzonitrile

269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: 3,5-dimethyl-4-hydroxybenzonitrile With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 0 - 5℃; for 0.166667h; Inert atmosphere;
Stage #2: 4-((4-amino-5-bromo-6-chloropyrimidin-2-yl)amino)benzonitrile In 1-methyl-pyrrolidin-2-one at 10 - 120℃; for 26.5h; Time; Temperature; Reagent/catalyst; Concentration; Inert atmosphere;		89%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 12h; Inert atmosphere;10 g
1616667-63-0

C25H22BrN5O3

269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: C25H22BrN5O3 With silver(II) fluoride Inert atmosphere; Glovebox;
Stage #2: With ammonia In water; isopropyl alcohol at 80℃; for 0.5h;
Stage #3: With hydrogenchloride In water at 0.25℃; for 0.5h;		56%
269055-76-7

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

269055-15-4

etravirine

Conditions
ConditionsYield
With ammonia In isopropyl alcohol41%
In water40.5%
In water40.5%
With ammonia In 1,4-dioxane at 150℃; for 96h; Sealed tube;0.44 g
329187-59-9

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

269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / Br2; NaHCO3 / H2O; methanol
2: 45 percent / N-methylpyrrolidine / dioxane
3: 41 percent / NH3 / propan-2-ol
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
2.1: ammonia / 1,4-dioxane; water / 12 h / 120 °C
3.1: bromine / dichloromethane / 4 h / 0 - 5 °C
3.2: pH 9 - 10
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
2.1: ammonium hydroxide / water; 1,4-dioxane / 12 h / 120 °C
3.1: bromine / dichloromethane / 4 h / 0 - 5 °C
3.2: pH 9-10
View Scheme
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / tetrahydrofuran / 20 °C
2: ammonia / 1,4-dioxane / 1 h / 50 °C / Sealed tube
3: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 80 °C / Inert atmosphere
View Scheme
374067-80-8

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

269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 86 percent / POCl3
2: 78 percent / Br2; NaHCO3 / H2O; methanol
3: 45 percent / N-methylpyrrolidine / dioxane
4: 41 percent / NH3 / propan-2-ol
View Scheme
Multi-step reaction with 4 steps
1.1: trichlorophosphate; N,N-dimethyl-aniline / 6 h / Reflux
2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
3.1: ammonia / 1,4-dioxane; water / 12 h / 120 °C
4.1: bromine / dichloromethane / 4 h / 0 - 5 °C
4.2: pH 9 - 10
View Scheme
Multi-step reaction with 4 steps
1.1: trichlorophosphate; N,N-dimethyl-aniline / 6 h / Reflux
2.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 45 °C
3.1: ammonium hydroxide / water; 1,4-dioxane / 12 h / 120 °C
4.1: bromine / dichloromethane / 4 h / 0 - 5 °C
4.2: pH 9-10
View Scheme
Multi-step reaction with 4 steps
1: trichlorophosphate / 12 h / 90 - 95 °C
2: N-Bromosuccinimide / tetrahydrofuran / 20 °C
3: ammonia / 1,4-dioxane / 1 h / 50 °C / Sealed tube
4: potassium carbonate / 1-methyl-pyrrolidin-2-one / 12 h / 80 °C / Inert atmosphere
View Scheme
269055-75-6

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

269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 45 percent / N-methylpyrrolidine / dioxane
2: 41 percent / NH3 / propan-2-ol
View Scheme

4-cyanophenyl guanidine hydrochloride

269055-15-4

etravirine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 76 percent / NaOEt / ethanol
2: 86 percent / POCl3
3: 78 percent / Br2; NaHCO3 / H2O; methanol
4: 45 percent / N-methylpyrrolidine / dioxane
5: 41 percent / NH3 / propan-2-ol
View Scheme
1030633-38-5

4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide

269055-15-4

etravirine

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 1.25h;

4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile

A

1030633-38-5

4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide

B

269055-15-4

etravirine

Conditions
ConditionsYield
Stage #1: 4-{6-amino-2-[(4-cyanophenyl)amino]pyrimidin-4-yloxy}-3,5-dimethylbenzenecarbonitrile With bromine; acetic acid at 20 - 80℃; for 4.25h;
Stage #2: With sodium hydroxide In water at 20℃;

Etravirine Chemical Properties


IUPAC Name: 4-[6-Amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile
Molecular Weight: 435.2767 [g/mol]
Molecular Formula: C20H15BrN6O
XLogP3-AA: 4.5
H-Bond Donor: 2
H-Bond Acceptor: 7 
Index of Refraction: 1.702
Molar Refractivity: 106.87 cm3
Molar Volume: 275.6 cm3 
Surface Tension: 86.2 dyne/cm
Density: 1.57 g/cm3
Flash Point: 339.3 °C
Enthalpy of Vaporization: 94.15 kJ/mol
Boiling Point: 637.4 °C at 760 mmHg
Vapour Pressure: 3.82E-16 mmHg at 25 °C
Appearance: White to Off-White Solid
Melting Point: 265°C (dec.)
Classification Code of Etravirine (CAS NO.269055-15-4): Anti-HIV Agents; Antiviral; Antiviral Agents
Product Categories: All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Non-nucleoside Reverse Transcriptase; Pharmaceuticals

Etravirine Uses

 Etravirine (CAS NO.269055-15-4), in combination with other anti-retrovirals, is indicated for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in antiretroviral treatment-experienced adult patients, who have evidence of viral replication and HIV-1 strains resistant to a non-nucleoside reverse transcriptase inhibitor (NNRTI) and other antiretroviral agents.

Etravirine Specification

  Etravirine (CAS NO.269055-15-4), its Synonyms are 4-(6-Amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile ; Intelence ; TMC 125 ; 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-benzonitrile ; Benzonitrile, 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl- .

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