(1E,4E)-N-(3-(tert-butyldimethylsilyloxy)propyl)-2-(2-(dimethylamino)ethylamino)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide

Base Information

• Chemical Name: (1E,4E)-N-(3-(tert-butyldimethylsilyloxy)propyl)-2-(2-(dimethylamino)ethylamino)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide
• CAS No.: 1384958-71-7
• Molecular Formula: C₃₈H₅₇N₅O₃Si
• Molecular Weight: 659.988
• Mol file: 1384958-71-7.mol

Synonyms:(1E,4E)-N-(3-(tert-butyldimethylsilyloxy)propyl)-2-(2-(dimethylamino)ethylamino)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide

Chemical Property of (1E,4E)-N-(3-(tert-butyldimethylsilyloxy)propyl)-2-(2-(dimethylamino)ethylamino)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1E,4E)-N-(3-(tert-butyldimethylsilyloxy)propyl)-2-(2-(dimethylamino)ethylamino)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide

There total 9 articles about (1E,4E)-N-(3-(tert-butyldimethylsilyloxy)propyl)-2-(2-(dimethylamino)ethylamino)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide 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:

[4-(pyrrolidin-1-ylcarbonyl)phenyl]boronic acid (389621-81-2) → (1E,4E)-N-(3-(tert-butyldimethylsilyloxy)propyl)-2-(2-(dimethylamino)ethylamino)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide (1384958-71-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 18 h / 100 °C

2.1: toluene / 2.5 h / Reflux

3.1: acetic acid; iron / 4 h / 20 - 85 °C

3.2: pH 9 - 10

4.1: dichloromethane / 72 h / 20 °C

5.1: lithium hydroxide / ethanol; water; tetrahydrofuran / 30 h / 0 - 20 °C

5.2: pH 3.5

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.83 h / 20 °C

6.2: 1.5 h / 20 °C

7.1: triethylamine / N,N-dimethyl-formamide / 5 h / 65 °C / sealed tube

With iron; sodium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

tert-butyl (1E,4E)-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepin-2-ylcarbamate (1268163-51-4) + N,N-dimethylethylenediamine (108-00-9) → (1E,4E)-N-(3-(tert-butyldimethylsilyloxy)propyl)-2-(2-(dimethylamino)ethylamino)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide (1384958-71-7)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 65 ℃; for 5h; sealed tube;

Reference yield:

4-bromo-2-nitrotoluene (60956-26-5) → (1E,4E)-N-(3-(tert-butyldimethylsilyloxy)propyl)-2-(2-(dimethylamino)ethylamino)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide (1384958-71-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: acetic anhydride; chromium(VI) oxide; sulfuric acid / 1 h / 0 - 10 °C

1.3: 0.75 h

2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 18 h / 100 °C

3.1: toluene / 2.5 h / Reflux

4.1: acetic acid; iron / 4 h / 20 - 85 °C

4.2: pH 9 - 10

5.1: dichloromethane / 72 h / 20 °C

6.1: lithium hydroxide / ethanol; water; tetrahydrofuran / 30 h / 0 - 20 °C

6.2: pH 3.5

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.83 h / 20 °C

7.2: 1.5 h / 20 °C

8.1: triethylamine / N,N-dimethyl-formamide / 5 h / 65 °C / sealed tube

With chromium(VI) oxide; sulfuric acid; acetic anhydride; iron; sodium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

4-bromo-2-nitrobenzaldehyde

4-bromo-2-nitrotoluene

tert-butyl (1E,4E)-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepin-2-ylcarbamate

N,N-dimethylethylenediamine

Downstream raw materials:

(1E,4E)-2-(2-(dimethylamino)ethylamino)-N-(3-hydroxypropyl)-N-propyl-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxamide