Taranabant

Base Information

• Chemical Name: Taranabant
• CAS No.: 701977-09-5
• Molecular Formula: C27H25ClF3N3O2
• Molecular Weight: 515.963
• European Community (EC) Number: 682-599-4
• UNII: X9U622S114
• DSSTox Substance ID: DTXSID60220464
• Nikkaji Number: J2.533.443D
• Wikipedia: Taranabant
• Wikidata: Q7685387
• NCI Thesaurus Code: C81420
• Pharos Ligand ID: P3CJJJ9V36VS
• Metabolomics Workbench ID: 149866
• ChEMBL ID: CHEMBL220360
• Mol file: 701977-09-5.mol

Synonyms:MK 0364;MK-0364;MK0364;N-(3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl)-2-methyl-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)propanamide;taranabant

Chemical Property of Taranabant

Chemical Property:

• Melting Point: 106.0-106.3 °C
• Boiling Point: 634.2 °C at 760 mmHg
• PKA: 14.55±0.46(Predicted)
• Flash Point: 337.4 °C
• PSA: 75.01000
• Density: 1.3 g/cm³
• LogP: 6.70498
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 515.1587392
• Heavy Atom Count: 36
• Complexity: 776

Purity/Quality:

99% ^*data from raw suppliers

Tranabant(MK-0364) 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(CC1=CC=C(C=C1)Cl)C2=CC=CC(=C2)C#N)NC(=O)C(C)(C)OC3=NC=C(C=C3)C(F)(F)F
• Isomeric SMILES: C[C@@H]([C@@H](CC1=CC=C(C=C1)Cl)C2=CC=CC(=C2)C#N)NC(=O)C(C)(C)OC3=NC=C(C=C3)C(F)(F)F
• Recent ClinicalTrials: An Eighteen Month Efficacy and Safety Study in Obese Patients (0364-020)(COMPLETED)
• Recent EU Clinical Trials: A Phase IIb/III Randomized, Placebo-Controlled Clinical Trial to Study the Safety and Efficacy of MK-0364 in Overweight and Obese Patients With Type 2 Diabetes Mellitus (T2DM)

Technology Process of Taranabant

There total 34 articles about Taranabant 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: 95.0%

N-[(1Z)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylprop-1-en-1-yl]-2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (876365-70-7) → taranabant (701977-09-5,701977-00-6)

Guidance literature:

With hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate; (R,S)-(di-t-butylphosphino)ferrocenyl-ethyldi-o-tolyl-phosphine; In 1,2-dichloro-ethane; at 80 ℃; for 18h; under 25858.1 Torr;

Reference yield: 94.0%

2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanoic acid (605680-62-4) + 3-[(1S,2S)-2-amino-1-(4-chlorobenzyl)propyl]benzonitrile hydrochloride → taranabant (701977-09-5,701977-00-6)

Guidance literature:

With 4-methyl-morpholine; 1,3,5-trichloro-2,4,6-triazine; In acetonitrile; at 50 ℃; for 4h; Inert atmosphere; Large scale;

DOI:10.1021/op700026n

Reference yield: 90.0%

3-{(1S,2S)-1-(4-chlorobenzyl)-2-[(2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanoyl)amino]propyl}benzamide (876365-72-9) → taranabant (701977-09-5,701977-00-6)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; In Isopropyl acetate; N,N-dimethyl-formamide; at 25 ℃; for 1.5h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/op800270e

upstream raw materials:

2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanoic acid

N-[3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]amine hydrochloride

3-(3-bromophenyl)-4-(4-chlorophenyl)butan-2-one

ethyl 2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanoate

Refernces

• 1、 -. "LIQUID PHARMACEUTICAL COMPOSITIONS FOR PARENTERAL ADMINISTRATION OF A SUBSTITUTED AMIDE". Page/Page column 12-13. . Retrieved 2009/05/28.
• 2、 Chen, G-Yi,Frey, Lisa F.,Shultz, Scott,Wallace, Debra J.,Marcantonio, Karen,Payack, Joeseph F.,Vazquez, Enrique,Springfield, Shawn A.,Zhou, George,Liu, Ping,Kieczykowski, Gerard R.,Chen, Alex M.,Phenix, Brian D.,Singh, Utpal,Strine, Jeff,Izzo, Brianne,Krska, Shane W.. "Catalytic, enantioselective synthesis of taranabant, a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity". . p. 616 - 623. Retrieved 2012/12/31.