benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide

Base Information

• Chemical Name: benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide
• CAS No.: 441796-09-4
• Molecular Formula: C₂₃H₂₀Br₂N₆O₄S
• Molecular Weight: 636.324
• Mol file: 441796-09-4.mol

Synonyms:benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide

Chemical Property of benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide

There total 13 articles about benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

N-[5-(4-bromophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-N'-benzyl-sulfamide (441796-08-3) + 5-Bromo-2-chloropyrimidine (32779-36-5) → benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide (441796-09-4)

Guidance literature:

N-[5-(4-bromophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-N'-benzyl-sulfamide; With sodium hydride; In tetrahydrofuran; mineral oil; for 0.166667h;

5-Bromo-2-chloropyrimidine; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.333333h;

DOI:10.1021/jm3009103

Reference yield: 26.0%

benzylsulfamide potassium salt + 5-(4-bromophenyl)-4-(2-((5-bromopyrimidin-2-yl)oxy)ethoxy)-6-fluoropyrimidine → benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide (441796-09-4)

Guidance literature:

With tetrabutyl ammonium fluoride; potassium carbonate; In dimethyl sulfoxide; at 100 - 105 ℃; for 1h;

Reference yield:

5-(4-bromophenyl)-4,6-dichloropyrimidine (146533-41-7) → benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide (441796-09-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dimethyl sulfoxide / 24 h / 20 °C

2.1: potassium tert-butylate / 1,2-dimethoxyethane / 24 h / 95 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h

3.2: 3.33 h / 20 - 60 °C

3.3: 20 °C

With potassium tert-butylate; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; dimethyl sulfoxide; mineral oil;

upstream raw materials:

N-[5-(4-bromophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-N'-benzyl-sulfamide

5-Bromo-2-chloropyrimidine

benzylamine

(4-bromo-phenyl)-acetic acid methyl ester

Downstream raw materials:

ACT-132577

Refernces

• 1、 Bolli, Martin H.,Boss, Christoph,Binkert, Christoph,Buchmann, Stephan,Bur, Daniel,Hess, Patrick,Iglarz, Marc,Meyer, Solange,Rein, Josiane,Rey, Markus,Treiber, Alexander,Clozel, Martine,Fischli, Walter,Weller, Thomas. "The discovery of N -[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy] ethoxy]-4-pyrimidinyl]- N ′-propylsulfamide (macitentan), an orally active, potent dual endothelin receptor antagonist". supporting information. p. 7849 - 7861. Retrieved 2012/10/29.
• 2、 -. "4-PYRIMIDINESULFAMIDE DERIVATIVE". Page/Page column 14-15. . Retrieved 2009/04/25.