5-[(Z)-(5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

Base Information

• Chemical Name: 5-[(Z)-(5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
• CAS No.: 326914-10-7
• Molecular Formula: C₂₂H₂₇ClN₄O₂
• Molecular Weight: 414.935
• UNII: 1C7AZL970U
• DSSTox Substance ID: DTXSID90648016
• Nikkaji Number: J2.437.282K
• Wikidata: Q27088889
• Pharos Ligand ID: T1JGT5ACRKQY
• Metabolomics Workbench ID: 151158
• ChEMBL ID: CHEMBL13485
• Mol file: 326914-10-7.mol

Synonyms:SU 11652;SU-11652;SU11652

Chemical Property of 5-[(Z)-(5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

Chemical Property:

• PSA: 77.23000
• LogP: 4.37810
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Very Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 414.1822538
• Heavy Atom Count: 29
• Complexity: 636

Purity/Quality:

97% ^*data from raw suppliers

SU11652 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCNC(=O)C1=C(NC(=C1C)C=C2C3=C(C=CC(=C3)Cl)NC2=O)C
• Isomeric SMILES: CCN(CC)CCNC(=O)C1=C(NC(=C1C)/C=C\2/C3=C(C=CC(=C3)Cl)NC2=O)C
• Uses: SU11652 is a cell-permeable pyrrole-indolinone that acts as a tyrosine kinase receptor & angiogenic inhibitor.

Technology Process of 5-[(Z)-(5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

There total 5 articles about 5-[(Z)-(5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-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:

piperidine (110-89-4) + 5-chloro-indolin-2-one (17630-75-0) + N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (356068-86-5) → 5-(5-Chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide (326914-10-7)

Guidance literature:

In ethanol;

Reference yield:

N,N-diethylethylenediamine (100-36-7) + 5-(5-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (356069-14-2) → SU11652 (326914-10-7)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm0204183

Reference yield:

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (253870-02-9) → SU11652 (326914-10-7)

Guidance literature:

Multi-step reaction with 2 steps

1: piperidine / ethanol / 60 °C

2: HOBt; EDC / dimethylformamide / 20 °C

With piperidine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0204183

upstream raw materials:

N,N-diethylethylenediamine

5-(5-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate