| Identification | Back Directory | [Name]
4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide | [CAS]
150727-06-3 | [Synonyms]
Bosentan USP RC A
BenzenesulfonaMide(II)
bosentan intermediate(II)
Bosentan Related CoMpound A
Bosentan Related Compound 3
Bosentan USP Related CoMpound A
4-tert-Butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2
N-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)-B
4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide
N-[6-CHLORO-5-(2-METHOXYPHENOXY) [2,2-BIPRIMIDIN]-4-(1,1-DIMETHYLETHYL) BENZENESULFONAMIDE
4-tert-Butyl-N-[6-chloro-5-(2-methoxy-phenoxy)
-[2,2']bipyrimidinyl-4-yl]-benzenesulfonamide
N-[6-Chloro-5-(2-methoxphenoxy)(2,2-bipyrimidine)4-4-yl]-(1,1-dimethylethyl)-benzenesulfonamide
n-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide
4-tert-Butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide
N-[6-CHLORO-5-(2-METHOXYPHENOXY)-(2,2-BIPYRIMIDINE)4-4-YL]-(1,1-DIMETHYLETHYL)-BENZENESULFONAMIDE
Benzenesulfonamide, N-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)-
N-[6-Chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)-(9CI)-benzenesulfonamide
Benzenesulfonamide, N-[6-Chloro-5-(2-Methoxyphenoxy)[2,2'-Bi-Pyrimidin]-4-Yl]-4-(1,1-Dimethylethyl)-(9ci)
Benzenesulfonamide, N-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)- (bosentan intermediate)
Bosentan USP Related Compound A: 4-(tert-Butyl)-N-[6-chloro-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl]benzenesulfonamide
Bosentan Related Compound A (15 mg) (4-(tert-butyl)-N-[6-chloro-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl] benzenesulfonamide) | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C25H24ClN5O4S | [MDL Number]
MFCD09751194 | [MOL File]
150727-06-3.mol | [Molecular Weight]
526.01 |
| Chemical Properties | Back Directory | [Appearance]
Light Pale Yellow Sold | [Melting point ]
212-214°C | [Boiling point ]
676.7±65.0 °C(Predicted) | [density ]
1.348±0.06 g/cm3(Predicted) | [storage temp. ]
-20?C Freezer | [solubility ]
DMSO (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
3.67±0.10(Predicted) | [color ]
White to Pale Yellow | [Major Application]
pharmaceutical (small molecule) | [InChI]
InChI=1S/C25H24ClN5O4S/c1-25(2,3)16-10-12-17(13-11-16)36(32,33)31-22-20(35-19-9-6-5-8-18(19)34-4)21(26)29-24(30-22)23-27-14-7-15-28-23/h5-15H,1-4H3,(H,29,30,31) | [InChIKey]
XKISWHVJIZSPSC-UHFFFAOYSA-N | [SMILES]
C1(S(NC2C(OC3=CC=CC=C3OC)=C(Cl)N=C(C3=NC=CC=N3)N=2)(=O)=O)=CC=C(C(C)(C)C)C=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
Light Pale Yellow Sold | [Uses]
An intermediate of Bosentan, which is a mixed endothelin receptor antagonist | [Synthesis]
In a flask equipped with a mechanical stirrer, thermometer, reflux condenser, dropping funnel and heating jacket, a solution of 4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine (105 g) and 4-(tert-butyl)benzenesulfonamide (64.1 g, 0.30 mol) in DMSO (525 mL) was added. To this suspension was added potassium carbonate (83 g, 0.60 mol). The reaction mixture was heated to 100-105 °C under stirring and maintained for 3-4 hours. The reaction progress was monitored by HPLC. After completion of the reaction, the solution was cooled to 20-25 °C. Water (875 mL) was added slowly dropwise over 10-15 minutes and stirring was continued for 1 hour. The precipitated solid was collected by filtration, washed with water (2 x 350 mL) and subsequently transferred to a mortar. Water (800 mL) and concentrated hydrochloric acid (50 mL) were added and stirred for 30 minutes. The precipitated solid was collected by filtration again and washed with water (2 × 200 mL) and acetone (2 × 175 mL) sequentially. The solid was dried under reduced pressure at 40±2 °C for 16-24 h to afford the milky white solid product N-[6-chloro-5-(2-methoxyphenoxy)[2,2'-dipyrimidin]-4-yl]-4-tert-butylbenzenesulfonamide in a yield of 157.8-158.7 g (100% yield). | [References]
[1] Organic Process Research and Development, 2011, vol. 15, # 6, p. 1382 - 1387
[2] Patent: WO2014/104904, 2014, A1. Location in patent: Page/Page column 13; 14
[3] Organic Process Research and Development, 2013, vol. 17, # 8, p. 1021 - 1026
[4] Patent: WO2012/73135, 2012, A1. Location in patent: Page/Page column 10
[5] Patent: WO2013/57545, 2013, A1. Location in patent: Paragraph 15 |
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