N-(4-ethylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide

Base Information

• Chemical Name: N-(4-ethylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide
• CAS No.: 1596340-71-4
• Molecular Formula: C₂₇H₂₆N₄O₅S₂
• Molecular Weight: 550.659
• Mol file: 1596340-71-4.mol

Synonyms:N-(4-ethylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide

Chemical Property of N-(4-ethylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-ethylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide

There total 8 articles about N-(4-ethylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide 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: 46.0%

{2-[3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzoylamino]thiazol-4-yl}acetic acid (1596340-69-0) + ethylamine (75-04-7,85404-22-4) → N-(4-ethylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide (1596340-71-4)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmc.2014.02.009

Reference yield:

3-hydroxy-5-(4-methanesulfonylphenoxy)benzoic acid methyl ester (752242-45-8) → N-(4-ethylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide (1596340-71-4)

Guidance literature:

Multi-step reaction with 7 steps

1: triethylamine / dichloromethane / 2 h / -78 °C

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 20 - 85 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / N,N-dimethyl-formamide; water / 18 h / 80 °C

4: sodium hydroxide / water; tetrahydrofuran; methanol / 20 °C

5: triethylamine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 20 °C

6: lithium hydroxide / water; tetrahydrofuran; methanol / 20 °C

7: triethylamine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.02.009

Reference yield:

3-(4-methanesulfonylphenoxy)-5-(3-methylpyridin-2-yl)benzoic acid methyl ester (1596340-67-8) → N-(4-ethylcarbamoylmethylthiazol-2-yl)-3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzamide (1596340-71-4)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide / water; tetrahydrofuran; methanol / 20 °C

2: triethylamine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 20 °C

3: lithium hydroxide / water; tetrahydrofuran; methanol / 20 °C

4: triethylamine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / dichloromethane / 20 °C

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.bmc.2014.02.009

upstream raw materials:

{2-[3-(4-methanesulfonylphenoxy)-5-(3-methylpyridine-2-yl)benzoylamino]thiazol-4-yl}acetic acid

ethylamine

3-hydroxy-5-(4-methanesulfonylphenoxy)benzoic acid methyl ester

3-(4-methanesulfonylphenoxy)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid methyl ester