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147536-97-8

Basic Information
CAS No.: 147536-97-8
Name: Bosentan
Article Data: 49
Cas Database
Molecular Structure:
Molecular Structure of 147536-97-8 (Bosentan)
Formula: C27H29N5O6S
Molecular Weight: 551.623
Synonyms: Actelion;Ro 47-0203;Ro 47-0203/039;Tracleer;p-tert-Butyl-N-[6-(2-hydroxyethoxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide;Benzenesulfonamide,4-(1,1-dimethylethyl)-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-;
EINECS: 643-099-1
Density: 1.326 g/cm3
Melting Point: 171-175°C(lit.)
Boiling Point: 742.3 ºC at 760 mmHg
Flash Point: 402.8 ºC
Solubility: N/A
Appearance: pale yellow to off-white solid
Hazard Symbols: Xi
Risk Codes: R36; R43
Safety:
Transport Information: N/A
PSA: 154.03000
LogP: 5.35770
Synthetic route
107-21-1

ethylene glycol

150727-06-3

4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide

147536-97-8

bosentan

Conditions
ConditionsYield
Stage #1: ethylene glycol; 4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide With sodium hydroxide In tetrahydrofuran at 60 - 65℃; for 12h;
Stage #2: With tartaric acid In tetrahydrofuran; water at 5 - 10℃; for 1h;
95.7%
With sodium hydroxide In tetrahydrofuran at 50 - 65℃; for 7h; Time;92%
Stage #1: ethylene glycol; 4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide With sodium hydroxide at 100℃; for 2h;
Stage #2: With DL-tartaric acid In tetrahydrofuran; water Reagent/catalyst; Cooling with ice;
88.3%

N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butylbenzenesulphonamide sodium salt

147536-97-8

bosentan

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 20 - 30℃; for 3h;95%
With hydrogenchloride In ethanol; water pH=3;116 g

4-[(1,1-dimethylethyl)-N-[6-(2-formyloxy)ethoxy]-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]benzenesulfonamide

147536-97-8

bosentan

Conditions
ConditionsYield
Stage #1: 4-[(1,1-dimethylethyl)-N-[6-(2-formyloxy)ethoxy]-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]benzenesulfonamide With water; sodium hydroxide In ethanol at 25 - 30℃; for 1h;
Stage #2: With hydrogenchloride In ethanol; water for 1h; pH=5.5;
93%
Stage #1: 4-[(1,1-dimethylethyl)-N-[6-(2-formyloxy)ethoxy]-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]benzenesulfonamide With sodium hydroxide In water at 25℃; for 1h;
Stage #2: In ethanol Reflux;
91.2%

bosentan p-toluenesulfonate

147536-97-8

bosentan

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water at 20 - 25℃; for 1h;93%

4-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide potassium salt

147536-97-8

bosentan

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 20℃; for 3h;90%
With hydrogenchloride In water; 4-methyl-2-pentanone at 75℃; Inert atmosphere;
With hydrogenchloride In water; 4-methyl-2-pentanone at 75℃;
With hydrogenchloride In water32 g
1334686-08-6

trifluoromethanesulfonic acid 2-[6-(4-tert-butylbenzenesulfonylamino)-5-(2-methoxyphenoxy)-[2,2']bipyrimidinyl-4-yloxy]ethyl ester

147536-97-8

bosentan

Conditions
ConditionsYield
Stage #1: trifluoromethanesulfonic acid 2-[6-(4-tert-butylbenzenesulfonylamino)-5-(2-methoxyphenoxy)-[2,2']bipyrimidinyl-4-yloxy]ethyl ester With ethanol; sodium hydroxide at 20℃; for 1h;
Stage #2: With hydrogenchloride In dichloromethane; water at 0℃; pH=3 - 3.5;
90%
Stage #1: trifluoromethanesulfonic acid 2-[6-(4-tert-butylbenzenesulfonylamino)-5-(2-methoxyphenoxy)-[2,2']bipyrimidinyl-4-yloxy]ethyl ester With sodium hydroxide In ethanol at 20℃; for 1h;
Stage #2: With hydrogenchloride In ethanol; dichloromethane; water pH=3 - 3.5;
90%

4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide potassium salt

107-21-1

ethylene glycol

147536-97-8

bosentan

Conditions
ConditionsYield
Stage #1: ethylene glycol With potassium carbonate In acetonitrile for 0.25h;
Stage #2: 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide potassium salt In acetonitrile at 80 - 85℃; for 12h; Temperature; Time; Solvent;
89%
Stage #1: ethylene glycol With sodium hydroxide In acetonitrile at 75 - 80℃; for 8 - 12h;
Stage #2: 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide potassium salt In acetonitrile for 12 - 14h;
Stage #3: With hydrogenchloride; water In acetonitrile at 25℃; for 2h; pH=2 - 3; Product distribution / selectivity;
Stage #1: 4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide potassium salt; ethylene glycol With barium(II) hydroxide In toluene at 110℃;
Stage #2: With hydrogenchloride In water pH=1 - 2; Product distribution / selectivity;

4-tert-butyl-N-(5-(2-methoxyphenoxy)-6-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide

147536-97-8

bosentan

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In methanol at 20℃; for 24h; Inert atmosphere;84%
1174918-31-0

bosentan potassium

147536-97-8

bosentan

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 20 - 30℃; pH=0.5 - 1;80.8%
1174918-30-9

4-tert-butyl-N-(5-(2-methoxyphenoxy)-6-(2-oxoethoxy)-2,2′-bipyrimidin-4-yl)benzenesulfonamide

147536-97-8

bosentan

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 5℃; Solvent;80%
With sodium tetrahydroborate In methanol at 0 - 20℃;80%
With sodium tetrahydroborate In methanol at 0 - 5℃;75%
Stage #1: 4-tert-butyl-N-(5-(2-methoxyphenoxy)-6-(2-oxoethoxy)-2,2′-bipyrimidin-4-yl)benzenesulfonamide With sodium tetrahydroborate In methanol at 0 - 5℃; for 2h;
Stage #2: With hydrogenchloride In methanol; water pH=2; Product distribution / selectivity;
With methanol; sodium tetrahydroborate for 4h;
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    Product Name: Bosentan Synonyms: 2'-bipyrimidin)-4-yl)-enoxy)(;benzenesulfonamide,4-(1,1-dimethylethyl)-n-(6-(2-hydroxyethoxy)-5-(2-methoxyph;ro47-0203;4-(tert-Butyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-[2,2'-bipyrimidin]-4-yl)benzene

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Chemistry


Molecular Formula: C27H29N5O6S
Molar mass: 551.61 g/mol
Index of Refraction: 1.607
Molar Refractivity: 143.699 cm3
Molar Volume: 416.023 cm3
Surface Tension: 60.676 dyne/cm
Density: 1.326 g/cm3
Flash Point: 402.754 °C
Enthalpy of Vaporization: 113.612 kJ/mol
Boiling Point: 742.342 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Appearance: Pale yellow to off-White solid
Product categories of Bosentan (CAS NO.147536-97-8): Bases & Related Reagents ;Pharmaceuticals; Nucleotides
XLogP3-AA: 3.8
H-Bond Donor: 2
H-Bond Acceptor: 11
IUPAC Name: 4-Tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]benzenesulfonamide
Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC2=C(C(=NC(=N2)C3=NC=CC=N3)OCCO)OC4=CC=CC=C4OC
InChI: InChI=1S/C27H29N5O6S/c1-27(2,3)18-10-12-19(13-11-18)39(34,35)32-23-22(38-21-9-6-5-8-20(21)36-4)26(37-17-16-33)31-25(30-23)24-28-14-7-15-29-24/h5-15,33H,16-17H2,1-4H3,(H,30,31,32) 
InChIKey: GJPICJJJRGTNOD-UHFFFAOYSA-N

Uses

  Bosentan (CAS NO.147536-97-8) can be used for intermediates and is a fine Chemical.It is indicated mainly for the treatment of pulmonary hypertension, and has been approved in the European Union also for reducing the number of new digital ulcers in patients with systemic sclerosis and ongoing digital ulcer disease.In the United States,it is indicated for the treatment of pulmonary arterial hypertension in patients with WHO Class II-IV symptoms, to improve exercise capacity and decrease the rate of clinical worsening.

Safety Profile

Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx and SOx.

Specification

  Bosentan (CAS NO.147536-97-8) can be called Tracleer ; 4-Tert-butyl-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl]benzenesulfonamide ; N-[6-(2-Hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide .It is a dual endothelin receptor antagonist important in the treatment of pulmonary artery hypertension (PAH). It is licensed in the European Union, the United States and other countries by Actelion Pharmaceuticals for the management of PAH under the trade name Tracleer.