2-chloro-6-fluoro-3-(3-oxo-piperazin-1-ylmethyl)-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide

Base Information

• Chemical Name: 2-chloro-6-fluoro-3-(3-oxo-piperazin-1-ylmethyl)-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide
• CAS No.: 874655-46-6
• Molecular Formula: C₂₃H₂₈ClFN₄O₂
• Molecular Weight: 446.952
• Mol file: 874655-46-6.mol

Synonyms:2-chloro-6-fluoro-3-(3-oxo-piperazin-1-ylmethyl)-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide

Chemical Property of 2-chloro-6-fluoro-3-(3-oxo-piperazin-1-ylmethyl)-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-chloro-6-fluoro-3-(3-oxo-piperazin-1-ylmethyl)-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide

There total 7 articles about 2-chloro-6-fluoro-3-(3-oxo-piperazin-1-ylmethyl)-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide 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: 50.0%

2-chloro-6-fluoro-3-chloromethyl-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide (874655-45-5) + 2-Ketopiperazine (5625-67-2) → 2-chloro-6-fluoro-3-(3-oxo-piperazin-1-ylmethyl)-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide (874655-46-6)

Guidance literature:

With triethylamine; In dichloromethane; acetonitrile; for 20h; Heating;

DOI:10.1080/00397910500281234

Reference yield:

2-chloro-6-fluoro-3-methyl-quinoline-4-carbonyl chloride → 2-chloro-6-fluoro-3-(3-oxo-piperazin-1-ylmethyl)-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide (874655-46-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.05 g / Et₃N / tetrahydrofuran / 0.5 h

2: 90 percent / NaH / various solvent(s) / 0.5 h / 150 °C / microwave irradiation

3: 47 percent / NBS; dibenzoyl peroxide / CCl₄ / Heating

4: 80 percent / oxalyl chloride / CHCl₃; dimethylformamide / 1 h / 60 °C

5: 50 percent / Et₃N / acetonitrile; CH₂Cl₂ / 20 h / Heating

With N-Bromosuccinimide; oxalyl dichloride; sodium hydride; triethylamine; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/00397910500281234

Reference yield:

2-chloro-6-fluoro-3-methyl-quinoline-4-carboxylic acid [(S)-1-cyclohexylethyl]amide (874655-42-2) → 2-chloro-6-fluoro-3-(3-oxo-piperazin-1-ylmethyl)-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide (874655-46-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / NaH / various solvent(s) / 0.5 h / 150 °C / microwave irradiation

2: 47 percent / NBS; dibenzoyl peroxide / CCl₄ / Heating

3: 80 percent / oxalyl chloride / CHCl₃; dimethylformamide / 1 h / 60 °C

4: 50 percent / Et₃N / acetonitrile; CH₂Cl₂ / 20 h / Heating

With N-Bromosuccinimide; oxalyl dichloride; sodium hydride; triethylamine; dibenzoyl peroxide; In tetrachloromethane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/00397910500281234

upstream raw materials:

2-chloro-6-fluoro-3-chloromethyl-quinoline-4-carboxylic acid [(S)-1-cyclohexyl-ethyl]-amide

2-Ketopiperazine

6-fluoro-2-methoxy-3-methyl-quinoline-4-carboxylic acid [(S)-1-cyclohexylethyl]-amide

2-chloro-6-fluoro-3-methyl-quinoline-4-carboxylic acid [(S)-1-cyclohexylethyl]amide

Refernces