4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide

Base Information

• Chemical Name: 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide
• CAS No.: 1247825-27-9
• Molecular Formula: C₂₂H₂₀Cl₂N₄O₂S₂
• Molecular Weight: 507.464
• Mol file: 1247825-27-9.mol

Synonyms:4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide

Chemical Property of 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide

There total 4 articles about 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide 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: 45.0%

N,N-dimethyl-3-(4-aminophenoxy)propylamine (62424-88-8) + methyl 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]thiophene-2-carboxylate (1395919-95-5) → 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide (1247825-27-9)

Guidance literature:

N,N-dimethyl-3-(4-aminophenoxy)propylamine; With trimethylaluminum; In dichloromethane; toluene; at -10 - 20 ℃; for 0.75h; Inert atmosphere;

methyl 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]thiophene-2-carboxylate; In dichloromethane; toluene; at 20 ℃; Reflux;

With hydrogenchloride; In dichloromethane; toluene; for 0.5h;

DOI:10.1021/ml200276j

Reference yield: 27.0%

→ 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide (1247825-27-9)

Guidance literature:

Reference yield:

methyl 4‐cyano‐5‐(methylthio)thiophene‐2‐carboxylate (175202-48-9) → 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide (1247825-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.83 h / 0 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 0.17 h / 150 °C / Microwave irradiation

3.1: trimethylaluminum / dichloromethane; toluene / 0.75 h / -10 - 20 °C / Inert atmosphere

3.2: 20 °C / Reflux

3.3: 0.5 h

With trimethylaluminum; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; isopropyl alcohol; toluene;

DOI:10.1021/ml200276j

upstream raw materials:

methyl 4‐cyano‐5‐(methylthio)thiophene‐2‐carboxylate

3,4,5-trichloropyridine

N,N-dimethyl-3-(4-aminophenoxy)propylamine

methyl 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]thiophene-2-carboxylate