Orantinib

Base Information

• Chemical Name: Orantinib
• CAS No.: 210644-62-5
• Deprecated CAS: 245036-27-5
• Molecular Formula: C18H18N2O3
• Molecular Weight: 310.3471
• Hs Code.: 2933990090
• NSC Number: 702827
• UNII: 9RL37ZZ665
• DSSTox Substance ID: DTXSID101017164
• Nikkaji Number: J1.250.198F,J1.373.758D
• Wikidata: Q27088210
• NCI Thesaurus Code: C1884
• Pharos Ligand ID: XM61G5TNKAX6
• Metabolomics Workbench ID: 153128
• ChEMBL ID: CHEMBL274654
• Mol file: 210644-62-5.mol

Synonyms:(Z)-3-(2,4-dimethyl-5-(2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrol-3-yl)-propionic acid;(Z)-3-(2,4-dimethyl-5-(2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrol-3-yl)propionic acid;5-((1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-propanoic acid;orantinib;SU 6668;SU-6668;SU006668;SU6668;TSU 68;TSU-68

Chemical Property of Orantinib

Chemical Property:

• Vapor Pressure: 8.68E-15mmHg at 25°C
• Boiling Point: 590.5°Cat760mmHg
• Flash Point: 310.9°C
• PSA: 82.19000
• Density: 1.328g/cm³
• LogP: 3.27940
• Storage Temp.: +2C to +8C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 310.13174244
• Heavy Atom Count: 23
• Complexity: 516

Purity/Quality:

99% ^*data from raw suppliers

SU 6668 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(NC(=C1CCC(=O)O)C)C=C2C3=CC=CC=C3NC2=O
• Isomeric SMILES: CC1=C(NC(=C1CCC(=O)O)C)/C=C\2/C3=CC=CC=C3NC2=O
• Recent ClinicalTrials: Orantinib In Combination With Transcatheter Arterial Chemoembolization In Patients With Unresectable Hepatocellular Carcinoma
• Recent NIPH Clinical Trials: ORIENTAL: ORantinib InvEstigatioN on TAce combination triaL
• Uses: PDGFR Tyrosine Kinase Inhibitor VI, SU6668 is a potent ATP-competitive inhibitor against tyrosine kinases.

Technology Process of Orantinib

There total 11 articles about Orantinib 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: 91.0%

2-oxoindole (59-48-3) + 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid (1133-96-6) → (Z)-5-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrol-3-propanoic acid (210644-62-5)

Guidance literature:

2-oxoindole; 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid; With sodium hydroxide; In water; at 50 ℃; for 4h;

With acetic acid; In ethanol; for 0.25h; Product distribution / selectivity; Heating / reflux;

Reference yield:

pyrrolidine (123-75-1) + 2-oxoindole (59-48-3) + 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid (1133-96-6) → (Z)-5-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrol-3-propanoic acid (210644-62-5)

Guidance literature:

With acetic acid; In ethanol;

Reference yield:

ethyl 5-(ethoxycarbonyl)-2,4-dimethyl-1H-pyrrole-3-propanoate (54278-10-3) → (Z)-5-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrol-3-propanoic acid (210644-62-5)

Guidance literature:

With hydrogenchloride; sodium hydroxide;

upstream raw materials:

2-oxoindole

3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid

pyrrolidine

tert-butyl 3,5-dimethyl-4-(2-methoxycarbonylethyl)-1H-pyrrole-2-carboxylate