N-Ethyl-N-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamide

Base Information

• Chemical Name: N-Ethyl-N-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamide
• CAS No.: 100632-58-4
• Molecular Formula: C20H32 N2 O4 S
• Molecular Weight: 396.551
• Hs Code.: 2935909550
• UNII: L3J9NB91E2
• DSSTox Substance ID: DTXSID00565028
• Nikkaji Number: J362.111A
• Wikidata: Q72475064
• Mol file: 100632-58-4.mol

Synonyms:100632-58-4;N-Ethyl-N-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamide;L3J9NB91E2;N-ethyl-N-heptyl-4-[4-(methanesulfonamido)phenyl]-4-oxobutanamide;UNII-L3J9NB91E2;N-Ethyl-N-heptyl-4-[(4-Mesylamino)phenyl]-4-oxobutanamide;Ibutilide fumarate impurity A [USP];N-Ethyl-N-heptyl-4-(4-(methylsulfonamido)-phenyl)-4-oxobutanamide;Benzenebutanamide, N-ethyl-n-heptyl-4-((methylsulfonyl)amino)-gamma-oxo-;Benzenebutanamide, N-ethyl-N-heptyl-4-[(methylsulfonyl)amino]-gamma-oxo-;N-ETHYL-N-HEPTYL-4-(4-METHANESULFONAMIDOPHENYL)-4-OXOBUTANAMIDE;n-ethyl-n-heptyl-4-((4-mesylamino)phenyl)-4-oxobutanamide;IJUIQGJHHJVHKP-UHFFFAOYSA-N;NIAPROOFTYPE4;N-Ethyl-N-heptyl-4-[(methylsulfonyl)amino]-gamma-oxo-benzenebutanamide;SCHEMBL9625141;DTXSID00565028;MFCD09839032;AKOS015914639;CS-0152147;D82017;A897383;IBUTILIDE FUMARATE IMPURITY A [USP IMPURITY];N-ethyl-N-heptyl-4-[(methylsulfonyl)amino]-g-oxo- benzenebutanamide;N-Ethyl-N-heptyl-4-{4-[(methanesulfonyl)amino]phenyl}-4-oxobutanamide;N-ethyl-N-heptyl-gamma-oxo-4-[(methylsulfonyl)amino]benzenebutanamide;BENZENEBUTANAMIDE, N-ETHYL-N-HEPTYL-4-((METHYLSULFONYL)AMINO)-.GAMMA.-OXO-

Chemical Property of N-Ethyl-N-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamide

Chemical Property:

• Melting Point: 102-103 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 566.1±60.0 °C(Predicted)
• PKA: 7.19±0.10(Predicted)
• PSA: 91.93000
• Density: 1.141±0.06 g/cm3(Predicted)
• LogP: 4.99370
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 396.20827868
• Heavy Atom Count: 27
• Complexity: 549

Purity/Quality:

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

1,4-DiketoIbutilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCN(CC)C(=O)CCC(=O)C1=CC=C(C=C1)NS(=O)(=O)C
• Uses: An intermediate for preparing optically pure Ibutilide fumarate (I155400).

Technology Process of N-Ethyl-N-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamide

There total 2 articles about N-Ethyl-N-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamide 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:

ethyl(heptyl)amine (66793-76-8) + 4-((methanesulfonyl)amino)-γ-oxobenzenebutanoic acid (100632-57-3) → N-<4-<4-(ethyl-n-heptylamino)-1,4-dioxo-butyl>phenyl>methanesulfonamide (100632-58-4)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1.) DMF, 1 h, 2.) RT, 18 h;

DOI:10.1021/jm00105a048

Reference yield:

N-phenylmethanesulfonamide (1197-22-4) → N-<4-<4-(ethyl-n-heptylamino)-1,4-dioxo-butyl>phenyl>methanesulfonamide (100632-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 19.1 g / AlCl₃ / CS₂ / 24 h / 20 - 55 °C

2: 1.) 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / 1.) DMF, 1 h, 2.) RT, 18 h

With aluminium trichloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In carbon disulfide;

DOI:10.1021/jm00105a048

Reference yield: 87.0%

N-<4-<4-(ethyl-n-heptylamino)-1,4-dioxo-butyl>phenyl>methanesulfonamide (100632-58-4) → ibutilide (100632-81-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jm00105a048

upstream raw materials:

ethyl(heptyl)amine

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

N-phenylmethanesulfonamide

Downstream raw materials:

LY-190147

ibutilide

N-<4-<4-(ethyl-n-heptylamino)-1-hydroxy-4-oxo-butyl>phenyl>methanesulfonamide

(R)-N-Ethyl-N-heptyl-4-hydroxy-4-(4-methanesulfonylamino-phenyl)-butyramide

Refernces

• 1、 Hester,Gibson,Cimini,Emmert,Locker,Perricone,Skaletzky,Sykes,West. "N-[(ω-amino-1-hydroxyalkyl)phenyl]methanesulfonamide derivatives with Class III antiarrhythmic activity". . p. 308 - 315. Retrieved 2007/10/02.