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Bosentan Basic information Product Name: Bosentan Synonyms: 2’-bipyrimidin)-4-yl)-enoxy)(;benzenesulfonamide,4-(1,1-dimethylethyl)-n-(6-(2-hydroxyethoxy)-5-(2-methoxyph;ro47-0203;ro47-0203/039;BOSENTAN;Ro-47-0203, 4-(1,1-dimethylethyl)-N-[6
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ethylene glycol
4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide
bosentan
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% |
bosentan
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 20 - 30℃; for 3h; | 95% |
With hydrogenchloride In ethanol; water pH=3; | 116 g |
bosentan
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
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol; water at 20 - 25℃; for 1h; | 93% |
bosentan
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 |
trifluoromethanesulfonic acid 2-[6-(4-tert-butylbenzenesulfonylamino)-5-(2-methoxyphenoxy)-[2,2']bipyrimidinyl-4-yloxy]ethyl ester
bosentan
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% |
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; |
bosentan
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In methanol at 20℃; for 24h; Inert atmosphere; | 84% |
bosentan potassium
bosentan
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane; water at 20 - 30℃; pH=0.5 - 1; | 80.8% |
4-tert-butyl-N-(5-(2-methoxyphenoxy)-6-(2-oxoethoxy)-2,2′-bipyrimidin-4-yl)benzenesulfonamide
bosentan
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; |
2,2-dimethyl-propionic acid 2-[6-(4-tert-butyl-benzenesulfonylamino)-5-(2-methoxy-phenoxy)-[2,2']-bipyrimidinyl-4-yloxy]-ethyl ester
bosentan
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% |
bosentan
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0 - 5℃; | 80% |
4-tert-butyl-N-[6-(2-hydroxyethoxy)-2-iodo-5-(2-methoxyphenoxy)-pyrimidin-4-yl]-benzenesulfonamide
2-(tributylstannyl)pyrimidine
bosentan
Conditions | Yield |
---|---|
With cesium fluoride; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane at 100 - 110℃; for 16h; Inert atmosphere; | 70% |
trifluoromethanesulfonic acid 4-(2-tert-butoxyethoxy)-6-(4-tert-butylbenzenesulfonylamino)-5-(2-methoxyphenoxy)pyrimidin-2-yl ester
2-(tributylstannyl)pyrimidine
bosentan
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% |
bosentan
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 |
N-[2-bromo-6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide
2-(tributylstannyl)pyrimidine
bosentan
Conditions | Yield |
---|---|
With cesium fluoride; bis(tri-t-butylphosphine)palladium(0) In N,N-dimethyl-formamide at 140 - 150℃; for 16h; Inert atmosphere; | 47% |
2-(5-(2-methoxy-phenoxy)-6-chloro-2-(pyrimidin-2-yl)pyrimidin-4-yloxy) ethanol
4-tert-butylbenzenesulphonamide
bosentan
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; |
ethylene glycol
4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine
bosentan
Conditions | Yield |
---|---|
With sodium 1.) DMSO, rt, 2.) 100 deg C; Multistep reaction; |
5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl) pyrimidine-4,6(1H, 5H)-dione
bosentan
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 |
sodium ethane-1,2-diolate
4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide
bosentan
Conditions | Yield |
---|---|
In ethylene glycol |
ethylene glycol
4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide
A
p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide
B
bosentan
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; |
bosentan
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane; water pH=1 - 2; Product distribution / selectivity; |
p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide
2-chloro-ethanol
bosentan
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℃; |
bosentan hydrochloride
bosentan
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol; water for 2h; pH=7; |
ethylene sulfite
p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide
bosentan
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 |
ethylene glycol
bosentan
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; |
sodium 2-hydroxyethoxide
4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide
A
p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide
B
bosentan
Conditions | Yield |
---|---|
In water; isopropyl alcohol at 115℃; for 5h; | A 5.88 %Chromat. B n/a |
2-methoxy-phenol
bosentan
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 |
(2-methoxyphenoxy)-malonic acid dimethyl ester
bosentan
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 |
pivaloyl chloride
bosentan
2,2-dimethyl-propionic acid 2-[6-(4-tert-butyl-benzenesulfonylamino)-5-(2-methoxy-phenoxy)-[2,2']-bipyrimidinyl-4-yloxy]-ethyl ester
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% |
2,5-dihydroxybenzoic acid.
bosentan
N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-pyrimidin-2-yl-pyrimidin-4-yl]-4-tert-butyl-benzenesulfonamide gentisic acid cocrystal
Conditions | Yield |
---|---|
In n-heptane; acetone at 55℃; for 2.33333h; Concentration; Solvent; Temperature; Time; Sonication; | 96% |
Conditions | Yield |
---|---|
In acetonitrile at 65℃; for 32h; Temperature; Solvent; | 95.5% |
Conditions | Yield |
---|---|
With potassium hydroxide for 4h; Thermodynamic data; Reflux; | 74% |
maleic acid
bosentan
Conditions | Yield |
---|---|
In ethyl acetate; acetone at 4 - 80℃; for 12h; Concentration; Time; Temperature; Solvent; | 63% |
In acetonitrile at 4 - 20℃; |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0℃; | 57% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide for 48h; | 38% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide for 60h; | 30% |
[4-(nitrooxy)methyl]benzoic acid pentafluorophenyl ester
bosentan
Conditions | Yield |
---|---|
With dmap; scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃; | 23% |
Conditions | Yield |
---|---|
With dmap; scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃; | 15% |
pyridine-2-carbonyl azide
bosentan
Conditions | Yield |
---|---|
With dmap In toluene at 100℃; |
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