Ipsapirone

Base Information

• Chemical Name: Ipsapirone
• CAS No.: 95847-70-4
• Molecular Formula: C₁₉H₂₃N₅O₃S
• Molecular Weight: 401.489
• UNII: 6J9B11MN0K
• DSSTox Substance ID: DTXSID4045688
• Nikkaji Number: J108.011C
• Wikipedia: Ipsapirone
• Wikidata: Q6065448
• NCI Thesaurus Code: C74391
• Pharos Ligand ID: KH1F1ATPDULW
• Metabolomics Workbench ID: 144595
• ChEMBL ID: CHEMBL8412
• Mol file: 95847-70-4.mol

Synonyms:2-(4-(4-(2-pyrimidinyl)-1-piperzinyl)butyl)-1,2-benzisothiazol-3-(2H)-one-1,1-dioxide HCl;ipsapirone;isapirone;TVX Q 7821;TVX-Q-7821

Chemical Property of Ipsapirone

Chemical Property:

• Vapor Pressure: 8.96E-16mmHg at 25°C
• Melting Point: 137-138°
• Boiling Point: 629.8°Cat760mmHg
• Flash Point: 334.7°C
• PSA: 95.09000
• Density: 1.345g/cm³
• LogP: 2.24510
• Storage Temp.: Store at RT
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 401.15216079
• Heavy Atom Count: 28
• Complexity: 638

Purity/Quality:

99%+, ^*data from raw suppliers

Ipsapirone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CCCCN2C(=O)C3=CC=CC=C3S2(=O)=O)C4=NC=CC=N4
• Uses: Ipsapirone is a selective SR-1A agonist.

Technology Process of Ipsapirone

There total 6 articles about Ipsapirone 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: 76.0%

2-(4-(piperazin-1-yl)butyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide + 2-fluoropyrimidine (31575-35-6) → ipsapirone (95847-70-4)

Guidance literature:

With potassium hydroxide; hydroxypropyl methylcellulose; In water; at 20 ℃;

DOI:10.1039/d1gc00128k

Reference yield: 27.0%

N-(2-pyridinyl)piperazine (20980-22-7) + 4-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)butyl methanesulfonate → ipsapirone (95847-70-4)

Guidance literature:

With potassium hydrogencarbonate; In toluene; at 95 - 100 ℃; for 22h;

Reference yield:

saccharin (81-07-2) → ipsapirone (95847-70-4)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / acetonitrile / 20 h / Reflux

2: sulfuric acid; water / acetonitrile / 75 - 80 °C

3: triethylamine / ethyl acetate / 20 h / 5 - 25 °C

4: potassium hydrogencarbonate / toluene / 22 h / 95 - 100 °C

With sulfuric acid; water; potassium carbonate; potassium hydrogencarbonate; triethylamine; In ethyl acetate; toluene; acetonitrile;

upstream raw materials:

saccharin

N-(2-pyridinyl)piperazine

8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane Bromide

1-(2-pyrimidyl)piperazine dihydrochloride

Refernces

• 1、 Ku?aga, Damian,Ja?kowska, Jolanta,Jasiński, Radomir. "Microwave-Assisted Solvent-Free Synthesis of Ipsapirone". . p. 1498 - 1504. Retrieved 2019/05/16.