1-(5-Isoquinolinesulfonyl)piperazine

Base Information

• Chemical Name: 1-(5-Isoquinolinesulfonyl)piperazine
• CAS No.: 84468-24-6
• Molecular Formula: C13H15 N3 O2 S
• Molecular Weight: 277.347
• Hs Code.: 2935009090
• European Community (EC) Number: 635-920-7
• DSSTox Substance ID: DTXSID60233438
• Nikkaji Number: J285.100H
• Wikidata: Q27164985
• ChEMBL ID: CHEMBL75773
• Mol file: 84468-24-6.mol

Synonyms:1-(5-isoquinolinesulfonyl)piperazine;C-I-QP

Chemical Property of 1-(5-Isoquinolinesulfonyl)piperazine

Chemical Property:

• Appearance/Colour: Pale Yellow Crystalline Solid
• Vapor Pressure: 4.97E-10mmHg at 25°C
• Boiling Point: 497.4°C at 760 mmHg
• Flash Point: 254.6°C
• PSA: 70.68000
• Density: 1.332g/cm³
• LogP: 2.17620
• Storage Temp.: −20°C
• Solubility.: DMSO, Methanol, Water
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 277.08849790
• Heavy Atom Count: 19
• Complexity: 401

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

HA-100 Dihydrochloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)S(=O)(=O)C2=CC=CC3=C2C=CN=C3
• Uses: Exhibited potent inhibition toward protein kinase C and cyclic nucleotide dependent protein kinases

Technology Process of 1-(5-Isoquinolinesulfonyl)piperazine

There total 3 articles about 1-(5-Isoquinolinesulfonyl)piperazine 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: 89.0%

piperazine (110-85-0) + 5-isoquinolinesulfonyl chloride (84468-15-5) → (5-isoquinolinylsulfonyl)piperazine (84468-24-6)

Guidance literature:

With potassium carbonate; In dichloromethane;

Reference yield: 56.0%

isoquinoline-5-sulfonyl chloride hydrochloride (105627-79-0) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → (5-isoquinolinylsulfonyl)piperazine (84468-24-6)

Guidance literature:

isoquinoline-5-sulfonyl chloride hydrochloride; 1-t-Butoxycarbonylpiperazine; With triethylamine; In dichloromethane; at 20 ℃; for 2h;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/c9cc09595k

Reference yield:

isoquinoline-5-sulfonic acid (27655-40-9) → (5-isoquinolinylsulfonyl)piperazine (84468-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 70 °C / Inert atmosphere

2: pyridine; triethylamine / acetonitrile / 2 h / -5 - 20 °C

With pyridine; thionyl chloride; triethylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.1c01255

upstream raw materials:

piperazine

5-isoquinolinesulfonyl chloride

isoquinoline-5-sulfonyl chloride hydrochloride

1-t-Butoxycarbonylpiperazine

Downstream raw materials:

1-benzoyl-4-(5-isoquinolinesulfonyl)piperazine hydrochloride

(E)-1-[4-(Isoquinoline-5-sulfonyl)-piperazin-1-yl]-4-phenyl-but-3-en-1-one; hydrochloride