Pazinaclone

Base Information

• Chemical Name: Pazinaclone
• CAS No.: 103255-66-9
• Molecular Formula: C25H23ClN4O4
• Molecular Weight: 478.935
• UNII: MHK03047IJ
• DSSTox Substance ID: DTXSID70869388
• Nikkaji Number: J389.344H
• Wikipedia: Pazinaclone
• Wikidata: Q7157014
• NCI Thesaurus Code: C96874
• Mol file: 103255-66-9.mol

Synonyms:2-(7-chloro-1,8-naphthyridin-2-yl)-3-((1,4-dioxa-8-azaspiro(4.5)dec-8-yl)carbonylmethyl)isoindolin-1-one;DN 2327;DN-2327;pazinaclone

Chemical Property of Pazinaclone

Chemical Property:

• Vapor Pressure: 3.79E-20mmHg at 25°C
• Melting Point: 238-239°
• Refractive Index: 1.709
• Boiling Point: 712.5 °C at 760 mmHg
• PKA: 1.62±0.30(Predicted)
• Flash Point: 384.7 °C
• PSA: 84.86000
• Density: 1.48 g/cm³
• LogP: 3.74320
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 478.1407829
• Heavy Atom Count: 34
• Complexity: 783

Purity/Quality:

99% ^*data from raw suppliers

Pazinaclone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC12OCCO2)C(=O)CC3C4=CC=CC=C4C(=O)N3C5=NC6=C(C=C5)C=CC(=N6)Cl
• Description: Pazinaclone is a nonbenzodiazepine partial agonist. Animal work has shown that it has anxiolytic and anticonvulsant activity. Pazinaclone does not, however, produce the sedative, muscle relaxant, or motor coordination effects seen with diazepam (Waka and Fukada 1991). Phase II clinical trials are currently under way in the United States, Europe, and Japan, which have so far demonstrated that it is well tolerated and seems to cause significantly less sedation than do benzodiazepines (Uchiumi et al. 1992).
• Uses: Anti-anxiety agent.

Technology Process of Pazinaclone

There total 10 articles about Pazinaclone 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: 80.0%

2,7-dichloro-1,8-naphthyridine (55243-02-2) + 3-(2-oxo-2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)isoindolin-1-one → 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one (103255-66-9,147724-30-9,151764-87-3)

Guidance literature:

With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201600107

Reference yield: 68.0%

N-(7-chloro-1,8-naphthyridin-2-yl)benzamide (104917-09-1) + 1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)propenone (79404-70-9) → 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one (103255-66-9,147724-30-9,151764-87-3)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In acetonitrile; at 80 ℃; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.8b04026

Reference yield: 64.0%

carbon monoxide (201230-82-2) + 2-chloro-7-amino-1,8-naphthyridine (15944-33-9) + 8-[(2E)-3-(2-iodophenyl)prop-2-enoyl]-1,4-dioxa-8-azaspiro[4.5]decane → 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)carbonylmethylisoindolin-1-one (103255-66-9,147724-30-9,151764-87-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; trifuran-2-yl-phosphane; caesium carbonate; In 1,4-dioxane; at 110 ℃; under 760 Torr;

DOI:10.1016/j.tetlet.2003.08.036

upstream raw materials:

carbon monoxide

2-chloro-7-amino-1,8-naphthyridine

3-oxo-2-(7-chloro-1,8-naphthyridin-2-yl)isoindoline-1-acetic acid

diethyl cyanophosphonate

Refernces

• 1、 -. "Preparation method of anti-anxiety drug pagoclone or pazinaclone". Paragraph 0029-0038. . Retrieved 2019/04/09.
• 2、 Liu, Cong,Zhang, Qi,Li, Hongbo,Guo, Shuangxi,Xiao, Bin,Deng, Wei,Liu, Lei,He, Wei. "Cu/Fe Catalyzed Intermolecular Oxidative Amination of Benzylic C-H Bonds". . p. 6208 - 6212. Retrieved 2016/05/09.