Macitentan impurity B

Base Information

• Chemical Name: Macitentan impurity B
• CAS No.: 441796-13-0
• Molecular Formula: C₁₈H₁₈Br₂N₆O₄S
• Molecular Weight: 574.253
• Mol file: 441796-13-0.mol

Synonyms:Macitentan impurity B;Macitentan impurity D

Chemical Property of Macitentan impurity B

Chemical Property:

• Boiling Point: 686.7±65.0 °C(Predicted)
• PKA: 6.90±0.50(Predicted)
• Density: 1.715±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

N-Despropyl-N-ethylMacitentan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-Despropyl-N-ethyl Macitentan is an impurity of Macitentan (M105005); a dual orally active and potent endothelin receptor antagonist used for pulmonary arterial hypertension.

Technology Process of Macitentan impurity B

There total 7 articles about Macitentan impurity B 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:

C14H17BrN4O4S (441796-12-9) + 5-Bromo-2-chloropyrimidine (32779-36-5) → C18H18Br2N6O4S (441796-13-0)

Guidance literature:

C₁₄H₁₇BrN₄O₄S; With sodium hydride; In tetrahydrofuran; mineral oil; for 0.25h;

5-Bromo-2-chloropyrimidine; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 60 ℃; for 2h;

DOI:10.1021/jm3009103

Reference yield:

(4-bromo-phenyl)-acetic acid methyl ester (41841-16-1) → C18H18Br2N6O4S (441796-13-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 5 h / 40 - 45 °C

1.2: 24 h / 20 - 32 °C

2.1: sodium / methanol / 18 h / 0 - 20 °C

2.2: 4 h / 20 °C

3.1: trichlorophosphate / N,N-dimethyl-aniline / 2 h / 130 °C

4.1: dimethyl sulfoxide / 48 h / 20 °C

5.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.17 h / 40 °C

5.2: 70 h / 100 °C

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h

6.2: 2 h / 60 °C

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

DOI:10.1021/jm3009103

Reference yield:

5-(4-bromophenyl)-4,6-dichloropyrimidine (146533-41-7) → C18H18Br2N6O4S (441796-13-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dimethyl sulfoxide / 48 h / 20 °C

2.1: potassium tert-butylate / 1,2-dimethoxyethane / 0.17 h / 40 °C

2.2: 70 h / 100 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h

3.2: 2 h / 60 °C

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

DOI:10.1021/jm3009103

upstream raw materials:

2-(4-bromophenyl)-acetic acid

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

2-(4-bromophenyl)-malonic acid dimethyl ester

5-(4-bromophenyl)-4,6-dihydroxypyrimidine

Refernces