Casopitant

Base Information

• Chemical Name: Casopitant
• CAS No.: 414910-27-3
• Molecular Formula: C30H35F7N4O2
• Molecular Weight: 616.622
• UNII: 3B03KPM27L
• DSSTox Substance ID: DTXSID40961762
• Nikkaji Number: J2.788.949B
• Wikipedia: Casopitant
• Wikidata: Q5049003
• NCI Thesaurus Code: C71635
• Pharos Ligand ID: 4FNC4UJHMQLK
• Metabolomics Workbench ID: 149872
• ChEMBL ID: CHEMBL1672054
• Mol file: 414910-27-3.mol

Synonyms:(2R,4S)-4-(4-acetylpiperazin-1-yl)-N-((1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl)-2-(4-fluoro-2-methylphenyl)-N-methylpiperidine-1-carboxamide methanesulfonate;1-piperidinecarboxamide, 4-(4-acetyl-1-piperazinyl)-N-((1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl)-2-(4-fluoro-2-methylphenyl)-N-methyl-, (2R,4S)-;casopitant;casopitant mesilate;casopitant mesylate;GW-679769;GW-679769B;GW679769;GW679769B;Rezonic

Chemical Property of Casopitant

Chemical Property:

• PSA: 47.10000
• LogP: 6.46800
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 616.26482351
• Heavy Atom Count: 43
• Complexity: 949

Purity/Quality:

99% ^*data from raw suppliers

ZUNRISA 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)F)C2CC(CCN2C(=O)N(C)C(C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCN(CC4)C(=O)C
• Isomeric SMILES: CC1=C(C=CC(=C1)F)[C@H]2C[C@H](CCN2C(=O)N(C)[C@H](C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCN(CC4)C(=O)C
• Recent ClinicalTrials: A Study Of IV Casopitant For The Prevention Of Chemotherapy Induced Nausea And Vomiting.
• Recent EU Clinical Trials: NKV110721, A Study of Single Dose Intravenous Casopitant in Combination with Ondansetron and Dexamethasone for the Prevention of Oxaliplatin-Induced Nausea and Vomiting
• Uses: Casopitant can be used in treatment of unipolar depression, anxiety, and insomnia disorders; prevention and treatment of nausea and vomiting; treatment of functional dyspepsia, irritable bowel syndrome, gastroesophageal reflux disease, and overactive bladder disease.

Technology Process of Casopitant

There total 3 articles about Casopitant 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: 58.0%

[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl](methyl)amine (334477-60-0) + bis(trichloromethyl) carbonate (32315-10-9) + C26H33FN4O3 → [14C]-Casopitant (414910-27-3) + C30H35F7N4O2 (1255085-80-3)

Guidance literature:

C₂₆H₃₃FN₄O₃; With samarium diiodide; In tetrahydrofuran; methanol; at -78 - 20 ℃; Inert atmosphere;

bis(trichloromethyl) carbonate; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl](methyl)amine; In dichloromethane; for 48h; optical yield given as %de; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2010.03.036

Reference yield:

N-acetylpiperidine (13889-98-0) + (2R)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-oxo-1-piperidinecarboxamide (414910-03-5) → (2R,4R)-4-(4-acetyl-1-piperazinyl)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-1-piperidinecarboxamide + [14C]-Casopitant (414910-27-3)

Guidance literature:

N-acetylpiperidine; (2R)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-oxo-1-piperidinecarboxamide; With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 23 ℃; for 24h;

With sodium hydrogencarbonate; In water; 1,2-dichloro-ethane;

Reference yield:

N-acetylpiperidine (13889-98-0) + (2R)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-oxo-1-piperidinecarboxamide (414910-03-5) → (2R,4R)-4-(4-acetyl-1-piperazinyl)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-1-piperidinecarboxamide + [14C]-Casopitant (414910-27-3) + C24H25F7N2O2

Guidance literature:

With sodium tetrahydroborate; formic acid; In acetonitrile; optical yield given as %de;

DOI:10.1021/op1000622

upstream raw materials:

N-acetylpiperidine

(2R)-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4-oxo-1-piperidinecarboxamide

[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl](methyl)amine

bis(trichloromethyl) carbonate

Refernces

• 1、 Lee, Sharon K.,Tambar, Uttam K.,Perl, Nicholas R.,Leighton, James L.. "Highly enantioselective formal aza-Diels-Alder reactions with acylhydrazones and Danishefsky's diene promoted by a silicon Lewis acid". experimental part. p. 4769 - 4774. Retrieved 2010/08/07.