Pagoclone

Base Information

• Chemical Name: Pagoclone
• CAS No.: 133737-32-3
• Molecular Formula: C₂₃H₂₂ClN₃O₂
• Molecular Weight: 407.9
• DSSTox Substance ID: DTXSID40869830
• Nikkaji Number: J481.630G
• Wikipedia: Pagoclone
• Wikidata: Q7124393
• NCI Thesaurus Code: C74529
• Metabolomics Workbench ID: 149326
• ChEMBL ID: CHEMBL2104745
• Mol file: 133737-32-3.mol

Synonyms:2-(7-chloro-1.8-naphthyridin-2-yl)-2,3-dihydro-3-(5-methyl-2-oxohexyl)-1H-isoindol-1-one;pagoclone;RP 62955

Chemical Property of Pagoclone

Chemical Property:

• Vapor Pressure: 1.53E-13mmHg at 25°C
• Boiling Point: 582.1°Cat760mmHg
• PKA: 1.62±0.30(Predicted)
• Flash Point: 305.9°C
• PSA: 63.16000
• Density: 1.273g/cm³
• LogP: 5.44510
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 407.1400546
• Heavy Atom Count: 29
• Complexity: 613

Purity/Quality:

97% ^*data from raw suppliers

Pagoclone >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCC(=O)CC1C2=CC=CC=C2C(=O)N1C3=NC4=C(C=C3)C=CC(=N4)Cl
• Recent ClinicalTrials: Exploratory Study of Pagoclone in Men With Premature Ejaculation.
• Uses: Anti-anxiety agent.

Technology Process of Pagoclone

There total 15 articles about Pagoclone 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: 82.0%

N-(7-chloro-1,8-naphthyridin-2-yl) 3-hydroxyindolinone + [(5-methyl-2-oxo)hexyl]triphenylphosphonium bromide (136604-91-6) → 2-(7-chloro-1,8-naphthyridine-2-yl)-3-(5-methyl-2-oxo-hexyl)-1-isoindolinone (133737-32-3,133737-33-4,133737-48-1)

Guidance literature:

[(5-methyl-2-oxo)hexyl]triphenylphosphonium bromide; With sodium carbonate; In water; xylene; at 20 ℃; for 0.5h;

N-(7-chloro-1,8-naphthyridin-2-yl) 3-hydroxyindolinone; In xylene; at 136 ℃; for 24h;

Reference yield: 76.0%

3-(5-methyl-2-oxohexyl)isoindolin-1-one + 2,7-dichloro-1,8-naphthyridine (55243-02-2) → 2-(7-chloro-1,8-naphthyridine-2-yl)-3-(5-methyl-2-oxo-hexyl)-1-isoindolinone (133737-32-3,133737-33-4,133737-48-1)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201600107

Reference yield: 15.0%

6-methyl-1-hepten-3-one (42809-49-4) + benzaldehyde (100-52-7) + 2-chloro-7-amino-1,8-naphthyridine (15944-33-9) → 2-(7-chloro-1,8-naphthyridine-2-yl)-3-(5-methyl-2-oxo-hexyl)-1-isoindolinone (133737-32-3,133737-33-4,133737-48-1)

Guidance literature:

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

DOI:10.1021/acs.orglett.8b04026

upstream raw materials:

(±)-2-[1-(7-chloro-1,8-naphthyridin-2-ylamino)-6-methyl-3-oxoheptyl]benzoic acid

[(5-methyl-2-oxo)hexyl]triphenylphosphonium bromide

5-Methyl-2-hexanone

2.6-diaminopyridine

Downstream raw materials:

(±)-2-[1-(7-chloro-1,8-naphthyridin-2-ylamino)-6-methyl-3-oxoheptyl]benzoic acid

Refernces

• 1、 -. "Preparation method of anti-anxiety drug pagoclone or pazinaclone". Paragraph 0029; 0030; 0031; 0032; 0033. . Retrieved 2019/04/09.
• 2、 -. "Methods for making 2-(7-chloro-1,8-naphthyridine-2-yl)-3-(5-methyl-2-oxo-hexyl)-1-isoindolinone". Page/Page column 6. . Retrieved 2010/01/31.