4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile

Base Information

• Chemical Name: 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile
• CAS No.: 380843-81-2
• Molecular Formula: C₂₅H₂₇Cl₂N₅O₃
• Molecular Weight: 516.427
• UNII: 8870T6W3VG
• Nikkaji Number: J1.678.419B
• Pharos Ligand ID: LB48ZPUBN97V
• ChEMBL ID: CHEMBL128158

Synonyms:N-Desmethyl bosutinib;380843-81-2;Bosutinib metabolite M5;8870T6W3VG;UNII-8870T6W3VG;4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-(3-piperazin-1-ylpropoxy)quinoline-3-carbonitrile;3-Quinolinecarbonitrile, 4-((2,4-dichloro-5-methoxyphenyl)amino)6-methoxy-7-(3-(1-piperazinyl)propoxy));4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(1-piperazinyl)propoxy]-3-quinolinecarbonitri;4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(1-piperazinyl)propoxy]-3-quinolinecarbonitrile;4-Phenylamino-3-quinolinecarbonitrile deriv. 31e;BDBM4556;CHEMBL128158;SCHEMBL15787982;4-(2,4-Dichloro-5-methoxyanilino)-6-methoxy-7-(3-piperazinopropoxy)quinoline-3-carbonitrile;4-(2,4-dichloro-5-methoxyphenylamino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile;4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-(3-piperazin-1-ylpropoxy)-3-quinolinecarbonitrile;4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(piperazin-1-yl)propoxy]quinoline-3-carbonitrile

Chemical Property of 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile

Chemical Property:

• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 515.1490951
• Heavy Atom Count: 35
• Complexity: 706

Purity/Quality:

98%2H ^*data from raw suppliers

4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(1-piperazinyl)propoxy]-3-quinolinecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=C(C=N2)C#N)NC3=CC(=C(C=C3Cl)Cl)OC)OCCCN4CCNCC4
• Uses: Proteolysis Targeting Chimera (PROTAC) is a novel approach to modern drug development programs that utilizes small compounds to target proteins for ubiquitination and degradation by proteasome. 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(1-piperazinyl)propoxy]-3-quinolinecarbonitrile is a PROTAC compound, which has the potential to target oncogenic BCR-ABL for degradation. 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(1-piperazinyl)propoxy]-3-quinolinecarbonitrile has also been employed in ligand-based pharmacophore modelling to identify c-Src inhibitors.

Technology Process of 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile

There total 6 articles about 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile 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: 81.0%

4-{3-[3-cyano-4-(2,4-dichloro-5-methoxyphenylamino)-6-methoxyquinolin-7-yloxy]propyl}-piperazine-1-carboxylic acid tert-butyl ester → 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile (380843-81-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 8h;

Reference yield: 50.0%

piperazine (110-85-0) + 7-(3-chloropropoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile (380844-49-5) → 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile (380843-81-2)

Guidance literature:

With sodium iodide; In 1,2-dimethoxyethane; at 95 ℃; for 1h; Inert atmosphere; Microwave irradiation;

Reference yield:

7-(3-chloro-propoxy)-4-chloro-6-methoxy-quinoline-3-carbonitrile (214470-68-5) → 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile (380843-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 46 percent / pyridine hydrochloride / 2-ethoxy-ethanol / 2.5 h / Heating

2: 48 percent / NaI / 1,2-dimethoxy-ethane / 20 h / 95 °C

With pyridine hydrochloride; sodium iodide; In 2-ethoxy-ethanol; 1,2-dimethoxyethane;

DOI:10.1021/jm0102250

upstream raw materials:

piperazine

7-(3-chloropropoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile

2,4-dichloro-5-methoxyaniline

7-(3-chloro-propoxy)-4-chloro-6-methoxy-quinoline-3-carbonitrile

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