Bosentan supplier | CasNO.147536-97-8

Name
Bosentan
EINECS 643-099-1
CAS No. 147536-97-8
Article Data49
CAS DataBase
Density 1.326 g/cm³
Solubility
Melting Point 171-175°C(lit.)
Formula C₂₇H₂₉N₅O₆S
Boiling Point 742.3 ºC at 760 mmHg
Molecular Weight 551.623
Flash Point 402.8 ºC
Transport Information
Appearance pale yellow to off-white solid
Safety
Risk Codes R36; R43
Molecular Structure
Hazard Symbols Xi
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]-;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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 water	32 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With pyridinium p-toluenesulfonate In methanol at 20℃; for 24h; Inert atmosphere;	84%

: 1174918-31-0
bosentan potassium

: 147536-97-8
bosentan

Conditions

Conditions	Yield
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

Conditions	Yield
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;

: 1374293-39-6
2,2-dimethyl-propionic acid 2-[6-(4-tert-butyl-benzenesulfonylamino)-5-(2-methoxy-phenoxy)-[2,2']-bipyrimidinyl-4-yloxy]-ethyl ester

: 147536-97-8
bosentan

Conditions

Conditions	Yield
Stage #1: 2,2-dimethyl-propionic acid 2-[6-(4-tert-butyl-benzenesulfonylamino)-5-(2-methoxy-phenoxy)-[2,2']-bipyrimidinyl-4-yloxy]-ethyl ester With water; sodium hydroxide In ethanol at 10 - 25℃; Stage #2: With hydrogenchloride In ethanol; water at 10 - 15℃; for 2h;	80%

: ethyl 2-(6-(4-tert-butylphenylsulfonamido)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yloxy)acetate

: 147536-97-8
bosentan

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 5℃;	80%

: 1206769-86-9
4-tert-butyl-N-[6-(2-hydroxyethoxy)-2-iodo-5-(2-methoxyphenoxy)-pyrimidin-4-yl]-benzenesulfonamide

: 153435-63-3
2-(tributylstannyl)pyrimidine

: 147536-97-8
bosentan

Conditions

Conditions	Yield
With cesium fluoride; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane at 100 - 110℃; for 16h; Inert atmosphere;	70%

: 1334686-05-3
trifluoromethanesulfonic acid 4-(2-tert-butoxyethoxy)-6-(4-tert-butylbenzenesulfonylamino)-5-(2-methoxyphenoxy)pyrimidin-2-yl ester

: 153435-63-3
2-(tributylstannyl)pyrimidine

: 147536-97-8
bosentan

Conditions

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide at 130℃; for 6h; Stille Coupling;	70%
tetrakis(triphenylphosphine) palladium(0) In ISOPROPYLAMIDE at 130℃; for 6h;	70%

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

: 147536-97-8
bosentan

Conditions

Conditions	Yield
Stage #1: N-[6-[2-(1,1-dimethylethoxy)ethoxy]-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide With formic acid at 85℃; for 1.5h; Stage #2: With potassium carbonate In methanol for 1h;	70%
Stage #1: N-[6-[2-(1,1-dimethylethoxy)ethoxy]-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide With formic acid at 85℃; for 1.5h; Stage #2: With potassium carbonate In methanol for 1h; Stage #3: With hydrogenchloride In methanol; water; ethyl acetate pH=3 - 3.5;	70%
With phosphoric acid In acetonitrile at 25℃; Product distribution / selectivity; Reflux;
Multi-step reaction with 2 steps 1.1: 4 h / 85 °C 2.1: sodium hydroxide / water / 1 h / 25 °C 2.2: Reflux View Scheme

: 1206769-81-4
N-[2-bromo-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide

: 153435-63-3
2-(tributylstannyl)pyrimidine

: 147536-97-8
bosentan

Conditions

Conditions	Yield
With cesium fluoride; bis(tri-t-butylphosphine)palladium(0) In N,N-dimethyl-formamide at 140 - 150℃; for 16h; Inert atmosphere;	47%

: 184779-15-5
2-(5-(2-methoxy-phenoxy)-6-chloro-2-(pyrimidin-2-yl)pyrimidin-4-yloxy) ethanol

: 6292-59-7
4-tert-butylbenzenesulphonamide

: 147536-97-8
bosentan

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide; glycine In 1,4-dioxane at 120℃; for 44h; Product distribution / selectivity;	31%
With potassium phosphate; copper(l) iodide; glycine In 1,4-dioxane at 120℃; for 44h; Product distribution / selectivity;	31%
With potassium phosphate In N,N-dimethyl acetamide at 20 - 100℃; for 18h; Product distribution / selectivity;
With potassium carbonate; tetrabutylammomium bromide In toluene at 100 - 110℃; for 15h;

: 107-21-1
ethylene glycol

: 150728-13-5
4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine

: potassium 4-tert-butylbenzenesulfonate

: 147536-97-8
bosentan

Conditions

Conditions	Yield
With sodium 1.) DMSO, rt, 2.) 100 deg C; Multistep reaction;

...Expand

: 150728-12-4
5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl) pyrimidine-4,6(1H, 5H)-dione

: 147536-97-8
bosentan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: POCl3, PCl5 / Heating 2: 2.) Na / 1.) DMSO, rt, 2.) 100 deg C View Scheme
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 4 h / Reflux 2.1: potassium hydroxide / acetone / 0.08 h / 30 °C 2.2: 6.5 h / 30 °C / Reflux 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 30 - 50 °C 3.2: 0.5 h / 30 °C 4.1: hydrogenchloride; water / 1 h 5.1: sodium tetrahydroborate; methanol / 4 h View Scheme
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 90 - 105 °C 2.1: potassium carbonate; tetrabutylammomium bromide / toluene / 50 °C / Reflux; Dean-Stark 3.1: sodium hydroxide / toluene / 55 °C 4.1: 4 h / 85 °C 5.1: sodium hydroxide / water / 1 h / 25 °C 5.2: Reflux View Scheme
Multi-step reaction with 3 steps 1.1: phosphorus pentachloride / toluene / 2 h / Reflux 2.1: sodium hydroxide 2.2: 3 h / 90 °C 3.1: sodium hydroxide / tetrahydrofuran / 7 h / 50 - 65 °C View Scheme

: 7388-28-5, 10604-71-4, 24768-69-2, 26915-75-3, 50856-01-4, 92004-30-3
sodium ethane-1,2-diolate

: 150727-06-3
4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide

: 147536-97-8
bosentan

Conditions

Conditions	Yield
In ethylene glycol

: 107-21-1
ethylene glycol

: 150727-06-3
4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide

A: 174227-14-6
p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide

B: 147536-97-8
bosentan

Conditions

Conditions	Yield
Stage #1: ethylene glycol With sodium hydroxide In tetrahydrofuran at 50℃; for 0.5h; Stage #2: 4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide In tetrahydrofuran at 50 - 65℃; for 12h;

...Expand

: bosentan barium

: 147536-97-8
bosentan

Conditions

Conditions	Yield
With hydrogenchloride In dichloromethane; water pH=1 - 2; Product distribution / selectivity;

: 174227-14-6
p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide

: 107-07-3
2-chloro-ethanol

: 147536-97-8
bosentan

Conditions

Conditions	Yield
Stage #1: p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide With sodium carbonate In N,N-dimethyl-formamide at 110 - 115℃; for 4h; Stage #2: 2-chloro-ethanol In N,N-dimethyl-formamide for 16h; Stage #3: With hydrogenchloride; water In N,N-dimethyl-formamide pH=2; Product distribution / selectivity;
Stage #1: p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide; 2-chloro-ethanol With potassium tert-butylate In N,N-dimethyl-formamide at 120℃; for 15h; Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide at 20 - 25℃; pH=2;
Stage #1: p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide With sodium carbonate In dimethyl sulfoxide; toluene at 105 - 110℃; Stage #2: 2-chloro-ethanol In dimethyl sulfoxide; toluene at 105 - 110℃; Stage #3: With hydrogenchloride In water; dimethyl sulfoxide; toluene at 20℃;

: 1196074-08-4
bosentan hydrochloride

: 147536-97-8
bosentan

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water for 2h; pH=7;

: 3741-38-6
ethylene sulfite

: 174227-14-6
p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide

: 147536-97-8
bosentan

Conditions

Conditions	Yield
Stage #1: ethylene sulfite; p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide With potassium carbonate; tetrabutylammomium bromide In butanone Reflux; Stage #2: With water; sodium hydroxide In ethyl acetate

: N-(6-chloro-5-(2-methoxyphenoxy))-[2,2'-bipyrimidinyl]-4-t-butyl benzenesulfonamide cesium salt

: 107-21-1
ethylene glycol

: 147536-97-8
bosentan

Conditions

Conditions	Yield
Stage #1: ethylene glycol With sodium carbonate; dmap at 60 - 65℃; for 3h; Stage #2: N-(6-chloro-5-(2-methoxyphenoxy))-[2,2'-bipyrimidinyl]-4-t-butyl benzenesulfonamide cesium salt In tetrahydrofuran for 135h; Product distribution / selectivity; Reflux;

: 7388-28-5, 10604-71-4, 24768-69-2, 26915-75-3, 50856-01-4, 92004-30-3
sodium 2-hydroxyethoxide

: 150727-06-3
4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide

A: 174227-14-6
p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide

B: 147536-97-8
bosentan

Conditions

Conditions	Yield
In water; isopropyl alcohol at 115℃; for 5h;	A 5.88 %Chromat. B n/a

...Expand

: 90-05-1
2-methoxy-phenol

: 147536-97-8
bosentan

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / toluene / 20 °C / Reflux 1.2: 3.5 h / 60 °C / Reflux 2.1: sodium ethanolate / methanol / 6 h / 0 - 35 °C 3.1: trichlorophosphate / 4 h / 103 - 105 °C 3.2: 20 - 80 °C 4.1: potassium carbonate / tetrabutylammomium bromide / toluene / 2 h / Reflux 5.1: isopropyl alcohol; water / 5 h / 115 °C View Scheme
Multi-step reaction with 6 steps 1.1: sodium hydroxide / toluene / 20 °C / Reflux 1.2: 3.5 h / 60 °C / Reflux 2.1: sodium ethanolate / methanol / 6 h / 0 - 35 °C 3.1: trichlorophosphate / 4 h / 103 - 105 °C 3.2: 20 - 80 °C 4.1: potassium carbonate / tetrabutylammomium bromide / toluene / 2 h / Reflux 5.1: water / 5 h / 115 °C 5.2: 1 h / 55 - 85 °C 6.1: hydrogenchloride / dichloromethane; water / 20 - 30 °C / pH 0.5 - 1 View Scheme

Yield

Multi-step reaction with 5 steps
1.1: sodium hydroxide / toluene / 20 °C / Reflux
1.2: 3.5 h / 60 °C / Reflux
2.1: sodium ethanolate / methanol / 6 h / 0 - 35 °C
3.1: trichlorophosphate / 4 h / 103 - 105 °C
3.2: 20 - 80 °C
4.1: potassium carbonate / tetrabutylammomium bromide / toluene / 2 h / Reflux
5.1: isopropyl alcohol; water / 5 h / 115 °C
View Scheme

Multi-step reaction with 6 steps
1.1: sodium hydroxide / toluene / 20 °C / Reflux
1.2: 3.5 h / 60 °C / Reflux
2.1: sodium ethanolate / methanol / 6 h / 0 - 35 °C
3.1: trichlorophosphate / 4 h / 103 - 105 °C
3.2: 20 - 80 °C
4.1: potassium carbonate / tetrabutylammomium bromide / toluene / 2 h / Reflux
5.1: water / 5 h / 115 °C
5.2: 1 h / 55 - 85 °C
6.1: hydrogenchloride / dichloromethane; water / 20 - 30 °C / pH 0.5 - 1
View Scheme

: 150726-89-9
(2-methoxyphenoxy)-malonic acid dimethyl ester

: 147536-97-8
bosentan

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium ethanolate / methanol / 6 h / 0 - 35 °C 2.1: trichlorophosphate / 4 h / 103 - 105 °C 2.2: 20 - 80 °C 3.1: potassium carbonate / tetrabutylammomium bromide / toluene / 2 h / Reflux 4.1: isopropyl alcohol; water / 5 h / 115 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium ethanolate / methanol / 6 h / 0 - 35 °C 2.1: trichlorophosphate / 4 h / 103 - 105 °C 2.2: 20 - 80 °C 3.1: potassium carbonate / tetrabutylammomium bromide / toluene / 2 h / Reflux 4.1: water / 5 h / 115 °C 4.2: 1 h / 55 - 85 °C 5.1: hydrogenchloride / dichloromethane; water / 20 - 30 °C / pH 0.5 - 1 View Scheme
Multi-step reaction with 6 steps 1.1: sodium methylate / methanol / 3 h / 25 - 30 °C 1.2: 3 h / 25 - 30 °C 2.1: trichlorophosphate / 4 h / Reflux 3.1: potassium hydroxide / acetone / 0.08 h / 30 °C 3.2: 6.5 h / 30 °C / Reflux 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 30 - 50 °C 4.2: 0.5 h / 30 °C 5.1: hydrogenchloride; water / 1 h 6.1: sodium tetrahydroborate; methanol / 4 h View Scheme

: 3282-30-2
pivaloyl chloride

: 147536-97-8
bosentan

: 1374293-39-6
2,2-dimethyl-propionic acid 2-[6-(4-tert-butyl-benzenesulfonylamino)-5-(2-methoxy-phenoxy)-[2,2']-bipyrimidinyl-4-yloxy]-ethyl ester

Conditions

Conditions	Yield
Stage #1: bosentan In dichloromethane at 20 - 25℃; for 1h; Stage #2: pivaloyl chloride In dichloromethane at 20 - 25℃; for 15h;	97.5%

: 490-79-9
2,5-dihydroxybenzoic acid.

: 147536-97-8
bosentan

: 1450829-49-8
N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide gentisic acid cocrystal

Conditions

Conditions	Yield
In n-heptane; acetone at 55℃; for 2.33333h; Concentration; Solvent; Temperature; Time; Sonication;	96%

: 74124-79-1
di(succinimido) carbonate

: 147536-97-8
bosentan

: C32H32N6O10S

Conditions

Conditions	Yield
In acetonitrile at 65℃; for 32h; Temperature; Solvent;	95.5%

: zinc(II) nitrate hexahydrate

: 64-17-5
ethanol

: 147536-97-8
bosentan

: C54H56N10O12S2Zn*2.5C2H6O

Conditions

Conditions	Yield
With potassium hydroxide for 4h; Thermodynamic data; Reflux;	74%

...Expand

: 110-16-7
maleic acid

: 147536-97-8
bosentan

: N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide maleic acid cocrystal

Conditions

Conditions	Yield
In ethyl acetate; acetone at 4 - 80℃; for 12h; Concentration; Time; Temperature; Solvent;	63%
In acetonitrile at 4 - 20℃;

: 838878-70-9
pentafluorophenol 4-nitroxybutyrate

: 147536-97-8
bosentan

: C31H34N6O10S

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃;	57%

: 959639-85-1
chloromethyl (4-(nitrooxy)butyl) carbonate

: 147536-97-8
bosentan

: C33H38N6O12S

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide for 48h;	38%

: 959639-82-8
1-chloro-ethyl 4-nitooxy-butyl carbonate

: 147536-97-8
bosentan

: C34H40N6O12S

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide for 60h;	30%

: 874446-96-5
[4-(nitrooxy)methyl]benzoic acid pentafluorophenyl ester

: 147536-97-8
bosentan

: C35H34N6O10S

Conditions

Conditions	Yield
With dmap; scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃;	23%

: 935472-60-9
4-(nitrooxy)butyl 4-nitrophenyl carbonate

: 147536-97-8
bosentan

: C32H36N6O11S

Conditions

Conditions	Yield
With dmap; scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃;	15%

: 4013-71-2
pyridine-2-carbonyl azide

: 147536-97-8
bosentan

: pyridin-2-ylcarbamic acid 2-[6-(4-tert-butyl-phenylsulfonylamino)-5-(2-methoxy-phenoxy)-2,2'-bipyrimidin-4-yloxy]-ethyl ester

Conditions

Conditions	Yield
With dmap In toluene at 100℃;

Bosentan Chemical Properties

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

Bosentan 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.

Bosentan Safety Profile

Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NO_x and SO_x.

Bosentan 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.

Product Name

Bosentan

Synthetic route

Bosentan Chemical Properties

Bosentan Uses

Bosentan Safety Profile

Bosentan Specification

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