4-bromo-N-α-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}-N-[2-(dimethylamino)ethyl]-N-methyl-L-phenylalaninamide

Base Information

• Chemical Name: 4-bromo-N-α-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}-N-[2-(dimethylamino)ethyl]-N-methyl-L-phenylalaninamide
• CAS No.: 1239705-16-8
• Molecular Formula: C₂₄H₂₈BrCl₂N₃O₂
• Molecular Weight: 541.315
• Mol file: 1239705-16-8.mol

Synonyms:

Chemical Property of 4-bromo-N-α-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}-N-[2-(dimethylamino)ethyl]-N-methyl-L-phenylalaninamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-bromo-N-α-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}-N-[2-(dimethylamino)ethyl]-N-methyl-L-phenylalaninamide

There total 5 articles about 4-bromo-N-α-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}-N-[2-(dimethylamino)ethyl]-N-methyl-L-phenylalaninamide 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: 40.0%

(S)-3-(4-bromophenyl)-2-(1-(2,4-dichlorophenyl)cyclopropanecarboxamido)propanoic acid (1373527-90-2) + N,N',N'-trimethylenediamine (142-25-6) → 4-bromo-N-α-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}-N-[2-(dimethylamino)ethyl]-N-methyl-L-phenylalaninamide (1239705-16-8)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jm300122u

Reference yield:

1-(2,4-dichlorophenyl)cyclopropane-1-carboxylic acid → 4-bromo-N-α-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}-N-[2-(dimethylamino)ethyl]-N-methyl-L-phenylalaninamide (1239705-16-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; HATU / acetonitrile / 1 h / 20 °C

2.1: sodium hydroxide / methanol / 18 h / 20 °C

2.2: pH 3

3.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 20 °C

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jm300122u

Reference yield:

(S)-ethyl 2-amino-3-(4-bromophenyl)propanoate hydrochloride (232276-00-5) → 4-bromo-N-α-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}-N-[2-(dimethylamino)ethyl]-N-methyl-L-phenylalaninamide (1239705-16-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; HATU / acetonitrile / 1 h / 20 °C

2.1: sodium hydroxide / methanol / 18 h / 20 °C

2.2: pH 3

3.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 20 °C

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jm300122u

upstream raw materials:

C₂₁H₂₀BrCl₂NO₃

(S)-ethyl 2-amino-3-(4-bromophenyl)propanoate hydrochloride

(S)-3-(4-bromophenyl)-2-(1-(2,4-dichlorophenyl)cyclopropanecarboxamido)propanoic acid

N,N',N'-trimethylenediamine