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CAS No.: | 269055-15-4 |
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Name: | 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3, 5 –dimethylbenzonitrile |
Article Data: | 20 |
Molecular Structure: | |
Formula: | C20H15BrN6O |
Molecular Weight: | 435.283 |
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-; |
EINECS: | 682-331-6 |
Density: | 1.57 g/cm3 |
Melting Point: | 265oC (dec.) |
Boiling Point: | 637.4 °C at 760 mmHg |
Flash Point: | 339.3 °C |
Appearance: | white to off-white solid |
etravirine
Conditions | Yield |
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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% |
4-((4-amino-5-bromo-6-chloropyrimidin-2-yl)amino)benzonitrile
3,5-dimethyl-4-hydroxybenzonitrile
etravirine
Conditions | Yield |
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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 |
C25H22BrN5O3
etravirine
Conditions | Yield |
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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% |
4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]-benzonitrile
etravirine
Conditions | Yield |
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With ammonia In isopropyl alcohol | 41% |
In water | 40.5% |
In water | 40.5% |
With ammonia In 1,4-dioxane at 150℃; for 96h; Sealed tube; | 0.44 g |
4-((4,6-dichloropyrimidin-2-yl)amino)benzonitrile
etravirine
Conditions | Yield |
---|---|
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 |
4-((4,6-dihydroxypyrimidine-2-yl)amino)benzonitrile
etravirine
Conditions | Yield |
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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 |
4-[[(5-bromo-4,6-dichloro)-2-pyrimidinyl]amino]benzonitrile
etravirine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 45 percent / N-methylpyrrolidine / dioxane 2: 41 percent / NH3 / propan-2-ol View Scheme |
etravirine
Conditions | Yield |
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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 |
4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide
etravirine
Conditions | Yield |
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With sodium hydroxide In water at 20℃; for 1.25h; |
A
4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile hydrobromide
B
etravirine
Conditions | Yield |
---|---|
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℃; |
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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 (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 (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- .