Cilansetron

Base Information

• Chemical Name: Cilansetron
• CAS No.: 120635-74-7
• Molecular Formula: C₂₀H₂₁N₃O
• Molecular Weight: 319.406
• UNII: 2J6DQ1U5B5
• DSSTox Substance ID: DTXSID40152951
• Nikkaji Number: J554.930B
• Wikipedia: Cilansetron
• Wikidata: Q5119931
• NCI Thesaurus Code: C76106
• Pharos Ligand ID: Y4GZCUSN1ZK4
• Metabolomics Workbench ID: 149315
• ChEMBL ID: CHEMBL2103778
• Mol file: 120635-74-7.mol

Synonyms:10-((2-methyl-1H-imidazol-1-yl)methyl)-5,6,8,9,10,11-hexahydro-4H-pyrido(3,2,1-jk)carbazol-11-one;cilansetron

Chemical Property of Cilansetron

Chemical Property:

• Vapor Pressure: 2.21E-14mmHg at 25°C
• Boiling Point: 600.6°Cat760mmHg
• Flash Point: 317°C
• PSA: 39.82000
• Density: 1.36g/cm³
• LogP: 3.53770
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 319.168462302
• Heavy Atom Count: 24
• Complexity: 509

Purity/Quality:

99% ^*data from raw suppliers

Cilansetron ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=CN1CC2CCC3=C(C2=O)C4=CC=CC5=C4N3CCC5
• Isomeric SMILES: CC1=NC=CN1C[C@H]2CCC3=C(C2=O)C4=CC=CC5=C4N3CCC5
• Uses: Treatment of irritable bowel syndrome.

Technology Process of Cilansetron

There total 5 articles about Cilansetron 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: 87.0%

2-methylimidazole (693-98-1) + d,l-10-<(dimethylamino)methyl>-5,6,8,9,10,11-hexahydro-4H-pyrido<3,2,1-jk>carbazol-11-one hydrochloride → 4,5,6,8,9,10-hexahydro-10-[(2-methyl-1H-imidazol-1-yl)methyl]-11H-pyrido-[3,2,1-jk]-carbazol-11-one (120635-47-4,120635-74-7)

Guidance literature:

In water; at 100 ℃; for 20h;

DOI:10.1021/jm00075a026

Reference yield:

2-methylimidazole (693-98-1) + N-ethyloxazolidine (1630-73-5) + 5,6,8,9,10,11-hexahydro-4H-pyrido<3,2,1-jk>carbazol-11-one (120635-49-6) → 4,5,6,8,9,10-hexahydro-10-[(2-methyl-1H-imidazol-1-yl)methyl]-11H-pyrido-[3,2,1-jk]-carbazol-11-one (120635-47-4,120635-74-7)

Guidance literature:

With methanesulfonic acid; In butan-1-ol; at 70 - 120 ℃; for 2.86667h;

Reference yield:

2-(oxazolidin-3-yl)ethanol (20073-50-1) + 2-methylimidazole (693-98-1) + 5,6,8,9,10,11-hexahydro-4H-pyrido<3,2,1-jk>carbazol-11-one (120635-49-6) → 4,5,6,8,9,10-hexahydro-10-[(2-methyl-1H-imidazol-1-yl)methyl]-11H-pyrido-[3,2,1-jk]-carbazol-11-one (120635-47-4,120635-74-7)

Guidance literature:

With methanesulfonic acid; In butan-1-ol; at 70 - 120 ℃; for 2.38333h;

upstream raw materials:

2-methylimidazole

N-ethyloxazolidine

5,6,8,9,10,11-hexahydro-4H-pyrido<3,2,1-jk>carbazol-11-one

2-(oxazolidin-3-yl)ethanol

Refernces

• 1、 -. "Formulations of adenosine a1 agonists". . . Retrieved 2008/06/13.
• 2、 Van Wijngaarden,Hamminga,Van Hes,Standaar,Tipker,Tulp,Mol,Olivier,De Jonge. "Development of high-affinity 5-HT3 receptor antagonists. Structure- affinity relationships of novel 1,7-annelated indole derivatives. 1". . p. 3693 - 3699. Retrieved 2007/10/02.