Girisopam

Base Information

• Chemical Name: Girisopam
• CAS No.: 82230-53-3
• Molecular Formula: C18H17ClN2O2
• Molecular Weight: 328.798
• NSC Number: 373736
• UNII: 2LP301A921
• DSSTox Substance ID: DTXSID70231642
• Nikkaji Number: J227.603H
• Wikipedia: Girisopam
• Wikidata: Q3491663
• NCI Thesaurus Code: C74182
• ChEMBL ID: CHEMBL1915065
• Mol file: 82230-53-3.mol

Synonyms:1-(3-chlorophenyl)-4-methyl-7,8-dimethoxy-5H-2,3-benzodiazepine;EGIS 5810;EGIS-5810;girisopam;GYKI 51189;GYKI-51189

Chemical Property of Girisopam

Chemical Property:

• Vapor Pressure: 5.34E-08mmHg at 25°C
• Boiling Point: 453.9°Cat760mmHg
• Flash Point: 228.3°C
• PSA: 43.18000
• Density: 1.23g/cm³
• LogP: 2.99780
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 328.0978555
• Heavy Atom Count: 23
• Complexity: 480

Purity/Quality:

99% ^*data from raw suppliers

GIRISOPAM 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN=C(C2=CC(=C(C=C2C1)OC)OC)C3=CC(=CC=C3)Cl

Technology Process of Girisopam

There total 9 articles about Girisopam 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: 65.0%

2-(acetonyl)-3'-(chloro)-4,5-di-(methoxy)-benzophenone (104278-22-0) → 1-(3-chloro-phenyl)-4-methyl-7,8-dimethoxy-5H-2,3-benzodiazepine (82230-53-3)

Guidance literature:

With hydrazine hydrate; In ethanol; at 20 ℃; for 16h;

DOI:10.1246/cl.130580

Reference yield:

4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (866252-52-0) → 1-(3-chloro-phenyl)-4-methyl-7,8-dimethoxy-5H-2,3-benzodiazepine (82230-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: cesium fluoride / acetonitrile / 10 h / 20 °C

2: hydrazine hydrate / ethanol / 16 h / 20 °C

With hydrazine hydrate; cesium fluoride; In ethanol; acetonitrile;

DOI:10.1246/cl.130580

Reference yield:

3,4-dimethoxyphenylacetone (776-99-8) + 3-chlorobenzoate (535-80-8) → 1-(3-chloro-phenyl)-4-methyl-7,8-dimethoxy-5H-2,3-benzodiazepine (82230-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tris(methyl salicylate)phoshate ester; trifluorormethanesulfonic acid / 0.33 h / 20 °C

2: hydrazine hydrate; sodium carbonate / ethanol / 0.17 h / 0 - 20 °C

With trifluorormethanesulfonic acid; tris(methyl salicylate)phoshate ester; sodium carbonate; hydrazine hydrate; In ethanol; 1: |Friedel-Crafts Acylation;

DOI:10.1039/c8ob00708j

upstream raw materials:

2-(acetonyl)-3'-(chloro)-4,5-di-(methoxy)-benzophenone

(3,4-Dimethoxyphenyl)acetic acid

C₁₈H₁₇ClO₅

C₁₇H₁₄Cl₂N₂O₂

Downstream raw materials:

3-Acetyl-1-(3-chlorphenyl)-4,5-dihydro-7,8-dimethoxy-4-methylen-3H-2,3-benzodiazepin

3-Acetyl-1-(3-chlorphenyl)-7,8-dimethoxy-4-methyl-3H-2,3-benzodiazepin

Refernces

• 1、 Okuma, Kentaro,Tanabe, Yukiko,Nagahora, Noriyoshi,Shioji, Kosei. "Synthesis of 2,3-benzodiazepines and 2,3-benzodiazepin-4-ones from arynes and β-diketones". . p. 1064 - 1073. Retrieved 2015/09/01.
• 2、 Bihel, Frédéric J.J.,Justiniano, Héléne,Schmitt, Martine,Hellal, Malik,Ibrahim, Mohamed A.,Lugnier, Claire,Bourguignon, Jean-Jacques. "New PDE4 inhibitors based on pharmacophoric similarity between papaverine and tofisopam". . p. 6567 - 6572. Retrieved 2011/12/04.