Itasetron

Base Information

• Chemical Name: Itasetron
• CAS No.: 123258-84-4
• Molecular Formula: C₁₆H₂₀N₄O₂
• Molecular Weight: 300.36
• UNII: 00S0D0OEKR
• DSSTox Substance ID: DTXSID9048803
• Nikkaji Number: J336.600F,J336.606E
• Wikidata: Q76393581,Q27231369
• NCI Thesaurus Code: C65990
• ChEMBL ID: CHEMBL2105109,CHEMBL4765211
• Mol file: 123258-84-4.mol

Synonyms:(endo-N-8-methyl-8-azabicyclo(3.2.1.)-oct-3-yl)-2,3-dihydro-2-oxo-1H-benzimidazol-1-carboxamide;DAU 6215;DAU-6215;itasetron;itasetron hydrochloride;N-(8-methyl-8-azabicyclo (3.2.1.)oct-3-yl)2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxamide;U 98079A;U-98079A

Chemical Property of Itasetron

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.35g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 300.15862589
• Heavy Atom Count: 22
• Complexity: 469

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCC1CC(C2)NC(=O)N3C4=CC=CC=C4NC3=O
• Isomeric SMILES: CN1[C@@H]2CC[C@H]1CC(C2)NC(=O)N3C4=CC=CC=C4NC3=O
• Recent ClinicalTrials: Effects of Food on the Bioavailability and Pharmacokinetic Profile of Itasetron After a Single Oral Dose in Healthy Male Subjects

Technology Process of Itasetron

There total 4 articles about Itasetron 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: 75.0%

3-endo-tropanamine (87571-88-8) + 2,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chloride (65657-53-6) → Itasetron (123258-84-4)

Guidance literature:

In tetrahydrofuran; for 3h;

DOI:10.1021/jm00170a009

Reference yield:

endo-8-methyl-8-azabicyclo [3.2.1]octan-3-amine + 2,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chloride (65657-53-6) → Itasetron (123258-84-4)

Guidance literature:

In tetrahydrofuran; hydrogenchloride; acetonitrile;

Reference yield:

1,3-dihydro-2H-benzimidazol-2-one (615-16-7) → Itasetron (123258-84-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / charcoal / tetrahydrofuran / 1.) reflux, 12 h

2: 75 percent / tetrahydrofuran / 3 h

With pyrographite; In tetrahydrofuran;

DOI:10.1021/jm00170a009

upstream raw materials:

3-endo-tropanamine

2,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chloride

1,3-dihydro-2H-benzimidazol-2-one

Refernces

• 1、 -. "Benzimidazoline-2-oxo-1-carboxylic acid compounds useful as 5-HT receptor antagonists". . . Retrieved 2008/06/13.
• 2、 Turconi, Marco,Nicola, Massimo,Quintero, Myrna Gil,Maiocchi, Luciano,Micheletti, Rosella,et al.. "Synthesis of a New Class of 2,3-Dihydro-2-oxo-1H-benzimidazole-1-carboxylic Acid Derivatives as Highly Potent 5-HT3 Receptor Antagonists". . p. 2101 - 2108. Retrieved 2007/10/02.