4-(2,4-Dichloro-5-methoxyanilino)-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile

Base Information

• Chemical Name: 4-(2,4-Dichloro-5-methoxyanilino)-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile
• CAS No.: 622368-88-1
• Molecular Formula: C₂₆H₂₈Cl₂N₄O₃
• Molecular Weight: 515.439
• DSSTox Substance ID: DTXSID80416201
• Nikkaji Number: J2.038.409C
• Wikidata: Q82225402
• Pharos Ligand ID: 28PL4AC5U4NQ
• ChEMBL ID: CHEMBL41465
• Mol file: 622368-88-1.mol

Synonyms:622368-88-1;4-((2,4-Dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(2-(1-methylpiperidin-4-yl)ethoxy)quinoline-3-carbonitrile;4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile;4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile;4-phenylamino-3-quinolinecarbonitrile 6;3-quinolinecarbonitrile 23;CHEMBL41465;SCHEMBL676569;BDBM6095;DTXSID80416201;4-(2,4-Dichloro-5-methoxyanilino)-6-methoxy-7-[2-(1-methylpiperidine-4-yl)ethoxy]quinoline-3-carbonitrile;4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]-3-quinolinecarbonitrile

Chemical Property of 4-(2,4-Dichloro-5-methoxyanilino)-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile

Chemical Property:

• Vapor Pressure: 5.75E-15mmHg at 25°C
• Boiling Point: 613.1°C at 760 mmHg
• Flash Point: 324.6°C
• PSA: 82.87000
• Density: 1.34g/cm³
• LogP: 5.64458
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 514.1538462
• Heavy Atom Count: 35
• Complexity: 716

Purity/Quality:

4-[(2,4-DICHLORO-5-METHOXYPHENYL)AMINO]-6-METHOXY-7-[2-(1-METHYL-4-PIPERIDINYL)ETHOXY]-3-QUINOLINECARBONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC(CC1)CCOC2=C(C=C3C(=C2)N=CC(=C3NC4=CC(=C(C=C4Cl)Cl)OC)C#N)OC

Technology Process of 4-(2,4-Dichloro-5-methoxyanilino)-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile

There total 9 articles about 4-(2,4-Dichloro-5-methoxyanilino)-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]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: 40.0%

2-(1-methyl-4-piperidyl)ethanol (21156-84-3) + 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile (622369-46-4) → 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]-3-quinolinecarbonitrile (622368-88-1)

Guidance literature:

2-(1-methyl-4-piperidyl)ethanol; With sodium hydride; In N,N-dimethyl-formamide; at 110 ℃; for 1h;

4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-fluoro-6-methoxy-3-quinolinecarbonitrile; In N,N-dimethyl-formamide; at 135 ℃;

DOI:10.1021/jm0499458

Reference yield:

4-chloro-7-hydroxy-6-methoxyquinolin-3-carbonitrile (263149-10-6) → 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]-3-quinolinecarbonitrile (622368-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Ph₃P; (NCO₂Et)2 / tetrahydrofuran

2: NaH / tetrahydrofuran

With sodium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2003.07.001

Reference yield:

3-fluoro-4-methoxyaniline (366-99-4) → 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]-3-quinolinecarbonitrile (622368-88-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 42 percent / toluene / 4.5 h / 100 - 110 °C

2.1: 77 percent / POCl₃ / 0.5 h / Heating

3.1: 69 percent / pyridine hydrochloride / 2-ethoxy-ethanol / 3 h / 120 °C

4.1: NaH / dimethylformamide / 1 h / 110 °C

4.2: 40 percent / dimethylformamide / 135 °C

With pyridine hydrochloride; sodium hydride; trichlorophosphate; In 2-ethoxy-ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm0499458

upstream raw materials:

2,4-dichloro-5-methoxyaniline

2-(1-methyl-4-piperidyl)ethanol

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

3-fluoro-4-methoxyaniline