Basimglurant

Base Information

• Chemical Name: Basimglurant
• CAS No.: 802906-73-6
• Molecular Formula: C18H13ClFN3
• Molecular Weight: 325.773
• UNII: 3110E3AO8S
• ChEMBL ID: CHEMBL3301626
• DSSTox Substance ID: DTXSID801025734
• Metabolomics Workbench ID: 152927
• NCI Thesaurus Code: C166619
• Nikkaji Number: J3.481.216K
• Pharos Ligand ID: HYB9BU5W91XT
• Wikidata: Q18209947
• Wikipedia: Basimglurant
• Mol file: 802906-73-6.mol

Synonyms:2-chloro-4-(1-(4-fluorophenyl)-2,5-dimethyl-1H-imidazol-4-ylethynyl)pyridine;basimglurant;RO4917523

Chemical Property of Basimglurant

Chemical Property:

• Melting Point: 132 - 135°C
• Boiling Point: 526.6±60.0 °C(Predicted)
• PKA: 5.27±0.70(Predicted)
• PSA: 30.71000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 4.07640
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 325.0782033
• Heavy Atom Count: 23
• Complexity: 465

Purity/Quality:

99%+, ^*data from raw suppliers

RG7090（Basimglurant） >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N=C(N1C2=CC=C(C=C2)F)C)C#CC3=CC(=NC=C3)Cl
• Recent ClinicalTrials: An Efficacy and Safety Study of Basimglurant in Patients With Trigeminal Neuralgia.
• Recent EU Clinical Trials: A Phase 2B, Multicenter, 30-week, Prospective, Cross-over, Doubleblind, Randomized, Placebo-controlled Study Followed by a 52-Week Open-label Extension Study to Evaluate the Efficacy and Safety of Basimglurant Adjunctive to Ongoing Anticonvulsive Therapy in Children, Adolescents, and Young Adults with Seizures Associated with Tuberous Sclerosis Complex
• Uses: Basimglurant is a potent, selective and orally available mGlu5 negative allosteric modulator for the treatment of mood disorders.

Technology Process of Basimglurant

There total 8 articles about Basimglurant 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: 93.0%

3-chloro-2-(2-chloropyridin-4-yl)-3-[1-(4-fluorophenyl)-2,5-dimethyl-1H-imidazol-4-yl]propenal → RO-4917523 (802906-73-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; water; at -15 - 5 ℃; for 1h;

DOI:10.1021/jm501642c

Reference yield: 19.0%

methyl iodide (74-88-4) → RO-4917523 (802906-73-6)

Guidance literature:

2-chloro-4-[1-(4-fluoro-phenyl)-2-methyl-1H-imidazol-4-ylethynyl]-pyridine; With lithium diisopropyl amide; In tetrahydrofuran; at -75 ℃; for 0.25h;

methyl iodide; In tetrahydrofuran; at -75 ℃; for 2h; Product distribution / selectivity;

Reference yield:

2-chloro-4-[1-(4-fluoro-phenyl)-2-methyl-1H-imidazol-4-ylethynyl]-pyridine + methyl iodide (74-88-4) → RO-4917523 (802906-73-6)

Guidance literature:

2-chloro-4-[1-(4-fluoro-phenyl)-2-methyl-1H-imidazol-4-ylethynyl]-pyridine; With lithium diisopropyl amide; In tetrahydrofuran; at -75 ℃; for 0.25h;

methyl iodide; In tetrahydrofuran; at -75 ℃; for 2h;

upstream raw materials:

methyl iodide

(Z)-2-acetylamino-3-dimethylamino-but-2-enoic acid ethyl ester

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

Downstream raw materials:

2-chloro-4-[1-(4-fluoro-phenyl)-2,5-dimethyl-1H-imidazol-4-ylethynyl]-pyridine mono-sulfate

Refernces

• 1、 Jaeschke, Georg,Kolczewski, Sabine,Spooren, Will,Vieira, Eric,Bitter-Stoll, Nadia,Boissin, Patrick,Borroni, Edilio,Büttelmann, Bernd,Ceccarelli, Simona,Clemann, Nicole,David, Beatrice,Funk, Christoph,Guba, Wolfgang,Harrison, Anthony,Hartung, Thomas,Honer, Michael,Huwyler, J?rg,Kuratli, Martin,Niederhauser, Urs,P?hler, Axel,Peters, Jens-Uwe,Petersen, Ann,Prinssen, Eric,Ricci, Antonio,Rueher, Daniel,Rueher, Marianne,Schneider, Manfred,Spurr, Paul,Stoll, Theodor,T?nnler, Daniel,Wichmann, Jürgen,Porter, Richard H.,Wettstein, Joseph G.,Lindemann, Lothar. "Metabotropic glutamate receptor 5 negative allosteric modulators: Discovery of 2-chloro-4-[1-(4-fluorophenyl)-2,5-dimethyl-1 H-imidazol-4-ylethynyl]pyridine (basimglurant, RO4917523), a promising novel medicine for psychiatric diseases". . p. 1358 - 1371. Retrieved 2015/03/04.
• 2、 -. "Imidazole derivatives". . . Retrieved 2008/06/13.