4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide Chemical Properties

Melting point:

212-214°C

Boiling point:

676.7±65.0 °C(Predicted)

Density 

1.348±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

3.67±0.10(Predicted)

color 

White to Pale Yellow

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

Safety Information

HS Code 

2935909550

4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide Usage And Synthesis

Chemical Properties

Light Pale Yellow Sold

Uses

An intermediate of Bosentan, which is a mixed endothelin receptor antagonist. Bosentan USP Related Compound A.

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

4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide(150727-06-3)Related Product Information

• tert-Butyl peroxyacetate
• 2-Butoxyethanol
• p-Anisidine
• Cyhalofop-butyl
• 4-Methoxybenzyl alcohol
• 4-Methoxybenzyl cyanide
• Diethylene glycol monobutyl ether
• tert-Butyl acetate
• 4-Methoxyphenol
• Anisole
• (Trifluoromethoxy)benzene
• tert-Butanol
• Guaiacol
• Butyl acetate
• Buprofezin
• p-Anisaldehyde
• Butyl acrylate
• 4-tert-Butylbenzenesulfonamide