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CAS No. : | 157212-55-0 | MDL No. : | MFCD09751188 |
Formula : | C27H31N5O7S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SXTRWVVIEPWAKM-UHFFFAOYSA-N |
M.W : | 569.63 | Pubchem ID : | 185462 |
Synonyms : |
Ro 47-0203
|
Chemical Name : | 4-(tert-Butyl)-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-[2,2'-bipyrimidin]-4-yl)benzenesulfonamide hydrate |
Num. heavy atoms : | 40 |
Num. arom. heavy atoms : | 24 |
Fraction Csp3 : | 0.26 |
Num. rotatable bonds : | 11 |
Num. H-bond acceptors : | 11.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 147.96 |
TPSA : | 163.26 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.39 cm/s |
Log Po/w (iLOGP) : | 3.43 |
Log Po/w (XLOGP3) : | 3.36 |
Log Po/w (WLOGP) : | 5.03 |
Log Po/w (MLOGP) : | 0.24 |
Log Po/w (SILICOS-IT) : | 3.24 |
Consensus Log Po/w : | 3.06 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 2.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -5.21 |
Solubility : | 0.00354 mg/ml ; 0.00000622 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.47 |
Solubility : | 0.000195 mg/ml ; 0.000000342 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -9.25 |
Solubility : | 0.00000032 mg/ml ; 0.0000000006 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.51 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P202-P201-P280-P308+P313-P405 | UN#: | N/A |
Hazard Statements: | H361 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | 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 115℃; for 4h; Stage #2: 2-chloro-ethanol In N,N-dimethyl-formamide for 16h; | A mixture of 5 (38.5 g, 0.075 mol) in dimethylformamide (450 ml), sodium carbonate(32.15 g, 0.303 mol) was heated to (∼115C) for 4 h. 2-Chloroethanol (30.53 g, 0.379 mol)was then added and the mixture was stirred for 16 h. Water (∼400 ml) was added and thereaction mixture was then acidified with 6N HCl to a pH ∼ 2.0. The reaction mixture wasstirred for 10 min and extracted with methylene chloride (700 ml). The organic layer wasseparated, and the aqueous layer was extracted with toluene (∼200 ml). The organic layerswere combined, dried over sodium sulfate and evaporated under reduced pressure. The solidresidue was dissolved in methanol (150 ml) and stirred for 30 min. The reaction mixturewas then added to water (200 ml) and stirred for 4 h. The solid which precipitated out wascollected and dried to afford bosentan 4. (36.0 g, 86% yield) as a solid, mp. 138-140C.HPLC Purity: 99.70%. Water content: 3.2% (w/w). MS: m/z: 552 (M-OH). 1H-NMR: δ1.29 (s, 9H), 3.86 (s, 2H), 3.94 (s, 3H), 4.57 (m, 2H), 4.88 (s,1H), 6.85 (m, 1H), 7.10 (m,2H), 7.15 (m, 1H), 7.41(m, 3H), 8.42 (d, 2H, J = 4.9 Hz), 9.0 (d, 2H, J = 4.9Hz). IR:3437.4, (NH), 1342 cm-1 (SO2).Anal. Calcd for C27H31N5O7S: C, 56.93; H, 5.49; N, 12.29. Found: C, 56.68; H, 5.25;N, 12.48. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: trichlorophosphate 2.1: potassium carbonate; tetrabutylammomium bromide / toluene 3.1: sodium hydroxide / toluene; dimethyl sulfoxide; water / 13 h / Reflux 4.1: sodium carbonate / N,N-dimethyl-formamide / 4 h / 115 °C 4.2: 16 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trichlorophosphate 2: potassium carbonate; tetrabutylammomium bromide / toluene 3: sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In formic acid Heating; | ||
Multi-step reaction with 2 steps 1: toluene; ethanol 2: sodium hydroxide / water; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / toluene; dimethyl sulfoxide 2: 2-chloro-ethanol; sodium carbonate / N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogen sulfate In ethanol; dichloromethane; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide 2: toluene; ethanol 3: sodium hydroxide / water; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydroxide / toluene / 2 h / Reflux; Dean-Stark; Large scale 1.2: 3 h / Reflux; Large scale 2.1: sodium ethanolate / methanol / 5 °C / Large scale 3.1: trichlorophosphate; sodium hydroxide / toluene; water / 103 - 105 °C 4.1: potassium carbonate; hydrogenchloride; ammonium hydroxide / water; ethanol; acetonitrile; Isopropyl acetate 5.1: hydrogenchloride / methanol; water; ethanol; acetonitrile | ||
Multi-step reaction with 6 steps 1.1: sodium hydroxide / toluene / 2 h / Reflux; Dean-Stark; Large scale 1.2: 3 h / Reflux; Large scale 2.1: sodium ethanolate / methanol / 5 °C / Large scale 3.1: trichlorophosphate; sodium hydroxide / toluene; water / 103 - 105 °C 4.1: potassium carbonate; tetrabutylammomium bromide / toluene; water / 5 h / Dean-Stark; Large scale 5.1: sodium hydroxide / toluene; dimethyl sulfoxide 6.1: 2-chloro-ethanol; sodium carbonate / N,N-dimethyl-formamide | ||
Multi-step reaction with 7 steps 1.1: sodium hydroxide / toluene / 2 h / Reflux; Dean-Stark; Large scale 1.2: 3 h / Reflux; Large scale 2.1: sodium ethanolate / methanol / 5 °C / Large scale 3.1: trichlorophosphate; sodium hydroxide / toluene; water / 103 - 105 °C 4.1: potassium carbonate; tetrabutylammomium bromide 5.1: sodium hydroxide 6.1: toluene; ethanol 7.1: sodium hydroxide / water; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In methanol; ethanol; water; acetonitrile |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; 2-chloro-ethanol In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: ammonium chloride / methanol / 20 - 25 °C 2: sodium ethanolate / methanol / 5 °C / Large scale 3: trichlorophosphate; sodium hydroxide / toluene; water / 103 - 105 °C 4: potassium carbonate; hydrogenchloride; ammonium hydroxide / water; ethanol; acetonitrile; Isopropyl acetate 5: hydrogenchloride / methanol; water; ethanol; acetonitrile | ||
Multi-step reaction with 6 steps 1: ammonium chloride / methanol / 20 - 25 °C 2: sodium ethanolate / methanol / 5 °C / Large scale 3: trichlorophosphate; sodium hydroxide / toluene; water / 103 - 105 °C 4: potassium carbonate; tetrabutylammomium bromide / toluene; water / 5 h / Dean-Stark; Large scale 5: sodium hydroxide / toluene; dimethyl sulfoxide 6: 2-chloro-ethanol; sodium carbonate / N,N-dimethyl-formamide | ||
Multi-step reaction with 7 steps 1: ammonium chloride / methanol / 20 - 25 °C 2: sodium ethanolate / methanol / 5 °C / Large scale 3: trichlorophosphate; sodium hydroxide / toluene; water / 103 - 105 °C 4: potassium carbonate; tetrabutylammomium bromide 5: sodium hydroxide 6: toluene; ethanol 7: sodium hydroxide / water; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: methanol / 0 - 5 °C 2: ammonium chloride / methanol / 20 - 25 °C 3: sodium ethanolate / methanol / 5 °C / Large scale 4: trichlorophosphate; sodium hydroxide / toluene; water / 103 - 105 °C 5: potassium carbonate; hydrogenchloride; ammonium hydroxide / water; ethanol; acetonitrile; Isopropyl acetate 6: hydrogenchloride / methanol; water; ethanol; acetonitrile | ||
Multi-step reaction with 7 steps 1: methanol / 0 - 5 °C 2: ammonium chloride / methanol / 20 - 25 °C 3: sodium ethanolate / methanol / 5 °C / Large scale 4: trichlorophosphate; sodium hydroxide / toluene; water / 103 - 105 °C 5: potassium carbonate; tetrabutylammomium bromide / toluene; water / 5 h / Dean-Stark; Large scale 6: sodium hydroxide / toluene; dimethyl sulfoxide 7: 2-chloro-ethanol; sodium carbonate / N,N-dimethyl-formamide | ||
Multi-step reaction with 8 steps 1: methanol / 0 - 5 °C 2: ammonium chloride / methanol / 20 - 25 °C 3: sodium ethanolate / methanol / 5 °C / Large scale 4: trichlorophosphate; sodium hydroxide / toluene; water / 103 - 105 °C 5: potassium carbonate; tetrabutylammomium bromide 6: sodium hydroxide 7: toluene; ethanol 8: sodium hydroxide / water; ethanol |