6-[Ethyl(phenyl)sulfamoyl]-N-[(2-methoxyphenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxamide

Base Information

• Chemical Name: 6-[Ethyl(phenyl)sulfamoyl]-N-[(2-methoxyphenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxamide
• CAS No.: 423136-40-7
• Molecular Formula: C₂₆H₂₅N₃O₅S
• Molecular Weight: 491.568
• DSSTox Substance ID: DTXSID50394365
• Wikidata: Q82193703
• ChEMBL ID: CHEMBL201839
• Mol file: 423136-40-7.mol

Synonyms:423136-40-7;EC-000.1911;Oprea1_750644;Sulfonamide-03 (SF-03);CHEMBL201839;SCHEMBL16387046;DTXSID50394365;HMS3536B09;6-[Ethyl(phenyl)sulfamoyl]-N-[(2-methoxyphenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxamide;EU-0065319;SR-01000586253;SR-01000586253-1;6-(ethylphenylsulfamoyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 2-methoxy-benzylamide

Chemical Property of 6-[Ethyl(phenyl)sulfamoyl]-N-[(2-methoxyphenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxamide

Chemical Property:

• Refractive Index: 1.639
• PSA: 120.44000
• Density: 1.332g/cm³
• LogP: 5.33750
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 491.15149208
• Heavy Atom Count: 35
• Complexity: 893

Purity/Quality:

SULFONAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(C1=CC=CC=C1)S(=O)(=O)C2=CC3=C(C=C2)NC=C(C3=O)C(=O)NCC4=CC=CC=C4OC

Technology Process of 6-[Ethyl(phenyl)sulfamoyl]-N-[(2-methoxyphenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxamide

There total 6 articles about 6-[Ethyl(phenyl)sulfamoyl]-N-[(2-methoxyphenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-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: 35.0%

6-(ethyl-phenyl-sulfamoyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (853139-10-3) + 2-methoxybenzylamine (6850-57-3) → 6-(ethylphenylsulfamoyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 2-methoxybenzylamide (423136-40-7)

Guidance literature:

at 180 ℃; for 0.5h; microwave irradiation;

DOI:10.1124/mol.105.010959

Reference yield:

4-amino-N-ethyl-N-phenylbenzene sulfonamide (50497-33-1) → 6-(ethylphenylsulfamoyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 2-methoxybenzylamide (423136-40-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / 1 h / 140 °C

2: 45 percent / p-chlorobenzoic acid / diphenyl ether / 2 h / 250 °C / microwave irradiation

3: 35 percent / 0.5 h / 180 °C / microwave irradiation

With para-chlorobenzoic acid; In diphenylether; 2: Gould-Jacob cyclization;

DOI:10.1016/j.bmcl.2005.10.050

Reference yield:

2-{[4-(ethyl-phenyl-sulfamoyl)-phenylamino]-methylene}-malonic acid diethyl ester (876303-57-0) → 6-(ethylphenylsulfamoyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 2-methoxybenzylamide (423136-40-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / p-chlorobenzoic acid / diphenyl ether / 2 h / 250 °C / microwave irradiation

2: 35 percent / 0.5 h / 180 °C / microwave irradiation

With para-chlorobenzoic acid; In diphenylether; 1: Gould-Jacob cyclization;

DOI:10.1016/j.bmcl.2005.10.050

upstream raw materials:

6-(ethyl-phenyl-sulfamoyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

2-methoxybenzylamine

2-{[4-(ethyl-phenyl-sulfamoyl)-phenylamino]-methylene}-malonic acid diethyl ester

4-amino-N-ethyl-N-phenylbenzene sulfonamide