Nifekalant

Base Information

• Chemical Name: Nifekalant
• CAS No.: 130636-43-0
• Molecular Formula: C19H27N5O5
• Molecular Weight: 405.454
• UNII: 5VZ7GZM43E
• DSSTox Substance ID: DTXSID9046495
• Wikipedia: Nifekalant
• Wikidata: Q671772
• NCI Thesaurus Code: C75132
• Pharos Ligand ID: VHRURMBNAVN2
• ChEMBL ID: CHEMBL360861
• Mol file: 130636-43-0.mol

Synonyms:1,3-dimethyl-6-((2-(N-(2-hydroxyethyl)-3-(4-nitrophenyl)propylamino)ethylamino)-2,4(1H),3H)-pyrimidinedione hydrochloride;MS 551;MS-551;nifekalant;nifekalant hydrochloride

Chemical Property of Nifekalant

Chemical Property:

• Appearance/Colour: Crystals from ethanol
• Vapor Pressure: 3.84E-15mmHg at 25°C
• Melting Point: 117.5-118.5ºC
• Boiling Point: 597.9 °C at 760 mmHg
• Flash Point: 315.4 °C
• PSA: 125.32000
• Density: 1.32 g/cm³
• LogP: 1.72940
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 405.20121898
• Heavy Atom Count: 29
• Complexity: 613

Purity/Quality:

98%,99%, ^*data from raw suppliers

NIFEKALANT 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=CC(=O)N(C1=O)C)NCCN(CCCC2=CC=C(C=C2)[N+](=O)[O-])CCO
• Recent ClinicalTrials: Nifekalant Versus Amiodarone in New-Onset Atrial Fibrillation After Cardiac Surgery
• Recent NIPH Clinical Trials: The Randomized Controlled Trial Evaluating Utility of Catheter Ablation Us ing ExTRa mapping for Atrial Fibrillation

Technology Process of Nifekalant

There total 10 articles about Nifekalant 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: 89.7%

1,3-dimethyl-6{2-[(hydroxymethyl)amino]ethylamino}-2,4-(1H,3H)-pyrimidinedione + (3-(4-nitrophenyl)propyl)-4-methylbenzene-1-sulfonate (130636-37-2) → 1,3-dimethyl-6-[2-(N-[2-hydroxyethyl]-3-[4-nitrophenyl]propylamino)ethylamino]-2,4(1H,3H)-pyrimidinedione (130636-43-0)

Guidance literature:

(3-(4-nitrophenyl)propyl)-4-methylbenzene-1-sulfonate; With sodium hydroxide; In ethanol; at 50 - 60 ℃; for 1h;

1,3-dimethyl-6{2-[(hydroxymethyl)amino]ethylamino}-2,4-(1H,3H)-pyrimidinedione; With p-toluenesulfonyl chloride; In dichloromethane; at 80 ℃; for 1h;

Reference yield:

aqueous potassium carbonate + 1,3-Dimethyl-6-[2-(methylsulfonyloxy)ethylamino]-2,4(1H,3H)-pyrimidinedione + Benzylsulfonic acid (100-87-8) → 1,3-dimethyl-6-[2-(N-[2-hydroxyethyl]-3-[4-nitrophenyl]propylamino)ethylamino]-2,4(1H,3H)-pyrimidinedione (130636-43-0)

Guidance literature:

With hydrogenchloride; potassium carbonate; In N-methyl-acetamide; acetonitrile;

Reference yield:

3-(4-nitrophenyl)-1-propanol (20716-25-0) → 1,3-dimethyl-6-[2-(N-[2-hydroxyethyl]-3-[4-nitrophenyl]propylamino)ethylamino]-2,4(1H,3H)-pyrimidinedione (130636-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CHCl₃ / 16 h / Ambient temperature

2: 85 percent / dioxane / 3 h / 90 - 100 °C

3: 1.) NaOH, 2.) p-toluenesulfonic acid monohydrate / 1.) methanol, 50 deg C, 2.) 80 deg C, 1 h

With pyridine; sodium hydroxide; toluene-4-sulfonic acid; In 1,4-dioxane; chloroform;

DOI:10.1021/jm00096a003

upstream raw materials:

N-(2-hydroxyethyl)-N-[3-(4-nitrophenyl)propyl]amine

1,3-dimethyl-6-[2-(p-toluenesulfonyloxy)ethylamino)-2,4(1H,3H)-pyrimidinedione

1,3-Dimethyl-6-chlorouracil

3-(4-nitrophenyl)-1-propanol

Downstream raw materials:

Shinbit

Refernces

• 1、 -. "Pyrimidinedione derivatives and antiarrhythmic agents containing same". . . Retrieved 2008/06/13.
• 2、 -. "Pyrimidinedione compounds, method of producing the same and antiarrythmic agents containing the same". . . Retrieved 2008/06/13.