trecetilide

Base Information

• Chemical Name: trecetilide
• CAS No.: 180918-68-7
• Molecular Formula: C₂₁H₃₇FN₂O₃S
• Molecular Weight: 416.601
• Mol file: 180918-68-7.mol

Synonyms:Methanesulfonamide,N-[4-[4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxybutyl]phenyl]-, (S)-;Trecetilide

Chemical Property of trecetilide

Chemical Property:

• PSA: 78.02000
• Density: 1.120
• LogP: 5.65590

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of trecetilide

There total 24 articles about trecetilide 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: 91.1%

C10H22FN + N-{4-[(2S)-5-hydroxytetrahydrofuran-2-yl]phenyl}methanesulfonamide → Trecetilide (180918-68-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; In ethyl acetate; at 0 - 23 ℃;

DOI:10.1021/op049799f

Reference yield: 80.0%

1-bromo-6-fluoro-6-methylheptane (135124-58-2) + (S)-(-)-N-[4-[4-(ethylamino)-1-hydroxybutyl]phenyl]methanesulfonamide (180918-70-1) → Trecetilide (180918-68-7)

Guidance literature:

With sodium hydrogencarbonate; In acetonitrile; for 16h; Heating;

DOI:10.1021/jm0004289

Reference yield:

6-hydroxy-6-methylheptyl THP ether (13129-62-9) → N-(4-(4-(Ethyl(6-fluoro-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide (135124-45-7,180918-68-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 83.6 percent / DAST / CH₂Cl₂ / 0.42 h / -78 - 0 °C

2: 82.2 percent / pyridinium tosylate / ethanol / 41 h / 20 °C

3: 72.3 percent / NBS; Ph₃P / benzene / 5.5 h / 0 - 20 °C

4: 62.3 percent / NaHCO₃ / acetonitrile / 16 h / Heating

With N-Bromosuccinimide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; triphenylphosphine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In ethanol; dichloromethane; acetonitrile; benzene;

DOI:10.1021/jm0004289

upstream raw materials:

1-bromo-6-fluoro-6-methylheptane

N-[4-[4-(ethylamino)-1-hydroxybutyl]phenyl]methanesulfonamide

6-hydroxy-6-methylheptyl THP ether

4-((methanesulfonyl)amino)-γ-oxobenzenebutanoic acid

Downstream raw materials:

N-(4-{4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide hemi-fumaric acid

Refernces

• 1、 Hester,Gibson,Buchanan,Cimini,Clark,Emmert,Glavanovich,Imbordino,LeMay,McMillan,Perricone,Squires,Walters. "Progress toward the development of a safe and effective agent for treating reentrant cardiac arrhythmias: Synthesis and evaluation of ibutilide analogues with enhanced metabolic stability and diminished proarrhythmic potential". . p. 1099 - 1115. Retrieved 2007/10/03.