N-(4-[2-(4-aminophenyl)ethyl]-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

Base Information

• Chemical Name: N-(4-[2-(4-aminophenyl)ethyl]-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide
• CAS No.: 737827-45-1
• Molecular Formula: C₂₂H₂₅N₃O₃S₂
• Molecular Weight: 443.591

Synonyms:N-(4-[2-(4-aminophenyl)ethyl]-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

Chemical Property of N-(4-[2-(4-aminophenyl)ethyl]-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-[2-(4-aminophenyl)ethyl]-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

There total 14 articles about N-(4-[2-(4-aminophenyl)ethyl]-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide 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: 54.0%

tert-butyl N-{4-[2-(2-(acetylamino)-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-4-yl)ethyl]phenyl}carbamate (737827-44-0) → N-(4-[2-(4-aminophenyl)ethyl]-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (737827-45-1)

Guidance literature:

tert-butyl N-{4-[2-(2-(acetylamino)-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-4-yl)ethyl]phenyl}carbamate; With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 5h; Inert atmosphere;

With sodium hydroxide; In water;

DOI:10.1016/j.bmc.2013.02.048

Reference yield:

ethyl 2-(acetylamino)-4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazole-5-carboxylate (737823-53-9) → N-(4-[2-(4-aminophenyl)ethyl]-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (737827-45-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 3 h / 20 °C / 3040.2 Torr / Inert atmosphere

2.1: tetrahydrofuran / 2 h / Inert atmosphere; Reflux

3.1: sodium hydroxide / ethanol / 5 h / Reflux

3.2: 20 °C / pH 4

4.1: pyridine / 0 - 20 °C / Inert atmosphere

5.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C / Inert atmosphere

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

7.1: potassium tert-butylate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

8.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 20 °C / 2280.15 Torr

9.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 7.1: |Wittig Olefination;

DOI:10.1016/j.bmc.2013.02.048

Reference yield:

ethyl 2-(acetylamino)-4-[2-(4-aminophenyl)ethyl]-1,3-thiazole-5-carboxylate → N-(4-[2-(4-aminophenyl)ethyl]-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (737827-45-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrahydrofuran / 2 h / Inert atmosphere; Reflux

2.1: sodium hydroxide / ethanol / 5 h / Reflux

2.2: 20 °C / pH 4

3.1: pyridine / 0 - 20 °C / Inert atmosphere

4.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide; dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

6.1: potassium tert-butylate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 20 °C / 2280.15 Torr

8.1: hydrogenchloride / 1,4-dioxane / 5 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 6.1: |Wittig Olefination;

DOI:10.1016/j.bmc.2013.02.048

upstream raw materials:

ethyl 2-(acetylamino)-4-(chloromethyl)-1,3-thiazole-5-carboxylate

ethyl 2-(acetylamino)-4-[(E)-2-(4-nitrophenyl)ethenyl]-1,3-thiazole-5-carboxylate

ethyl 2-(acetylamino)-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}-ethyl)-1,3-thiazole-5-carboxylate

2-(acetylamino)-4-(2-{4-[(tert-butoxycarbonyl)-amino]phenyl}ethyl)-1,3-thiazole-5-carboxylic acid

Downstream raw materials:

N-{4-[2-(4-{[amino(imino)methyl]amino}phenyl)ethyl]-5-[2-[4-(methylsulfonyl)phenyl]ethyl]-1,3-thiazol-2-yl}acetamide hydrochloride

tert-butyl {(E)-({4-[2-(2-acetamido-5-{2-[4-(methylsulfonyl)phenyl]ethyl}-1,3-thiazol-4-yl)ethyl]phenyl}amino)[(tert-butoxycarbonyl)amino]methylene}carbamate

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