7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

Base Information

• Chemical Name: 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide
• CAS No.: 313740-83-9
• Molecular Formula: C₃₉H₅₁N₃O₄
• Molecular Weight: 625.852
• DSSTox Substance ID: DTXSID00388375
• Nikkaji Number: J2.031.071E
• Mol file: 313740-83-9.mol

Synonyms:7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide;313740-83-9;SCHEMBL6340941;DTXSID00388375;SJRPXPGYZYXHFY-UHFFFAOYSA-N;1H-1-Benzazepine-4-carboxamide, 2,3-dihydro-1-propyl-N-[4-[[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-7-[4-(2-butoxyethoxy)phenyl]-;7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[methyl(tetrahydropyran-4-yl)amino]methyl]phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxamide;7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide;7-{4-[2-(butoxy)ethoxy]phenyl}-N-(4{[methyl(tetrahydro-2h-pyran-4-yl)amino]methyl}phenyl)1-propyl-2,3-dihydro-1h-1-benzazepine-4-carboxamide;N-[4-[[Methyl(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-1-propyl-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

Chemical Property of 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

Chemical Property:

• XLogP3: 7.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 15
• Exact Mass: 625.38795712
• Heavy Atom Count: 46
• Complexity: 907

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCOCCOC1=CC=C(C=C1)C2=CC3=C(C=C2)N(CCC(=C3)C(=O)NC4=CC=C(C=C4)CN(C)C5CCOCC5)CCC

Technology Process of 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

There total 32 articles about 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-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: 50.0%

4-(2-butoxyethoxy)phenyl borate + 7-bromo-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (313728-79-9) → 7-{4-[2-(butoxy)ethoxy]phenyl}-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (313740-83-9)

Guidance literature:

4-(2-butoxyethoxy)phenyl borate; 7-bromo-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide; With potassium carbonate; In ethanol; water; toluene; at 20 ℃; for 0.5h;

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; water; toluene; for 10h; Heating / reflux;

Reference yield: 50.0%

{4-[2-(butoxy)ethoxy]phenyl}boronic acid (279262-28-1) + 7-bromo-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (313728-79-9) → 7-{4-[2-(butoxy)ethoxy]phenyl}-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (313740-83-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; toluene; Heating;

DOI:10.1248/cpb.52.577

Reference yield:

1-(3-propyl)-pyrrolidin-2-one (3470-99-3) → 7-{4-[2-(butoxy)ethoxy]phenyl}-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (313740-83-9)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydroxide; water / 8 h / Reflux

2: sodium carbonate / water; dimethyl sulfoxide / 4 h / Reflux

3: potassium carbonate / N,N-dimethyl-formamide / 1 h / 25 - 40 °C

4: sodium methylate / N,N-dimethyl-formamide; methanol / 0.5 h / 50 °C

5: palladium diacetate; triphenylphosphine; potassium phosphate / tetrahydrofuran / 5.5 h / 20 °C / Reflux; Inert atmosphere

6: sodium hydroxide; water / methanol; tetrahydrofuran / 3 h / Reflux

7: thionyl chloride / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / 20 - 30 °C

8: triethylamine / N,N-dimethyl-formamide; tetrahydrofuran / 1.5 h / 45 - 55 °C

With potassium phosphate; thionyl chloride; water; sodium methylate; palladium diacetate; sodium carbonate; potassium carbonate; triethylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 4: |Claisen Condensation / 5: |Suzuki-Miyaura Coupling;

DOI:10.1021/op0497916

upstream raw materials:

{4-[2-(butoxy)ethoxy]phenyl}boronic acid

7-bromo-N-(4-{[methyl(tetrahydro-2H-pyran-4-yl)amino]methyl}phenyl)-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide

4-bromo-phenol

1-(2-chloroethoxy)butane

Refernces

• 1、 Seto, Masaki,Aramaki, Yoshio,Okawa, Tomohiro,Miyamoto, Naoki,Aikawa, Katsuji,Kanzaki, Naoyuki,Niwa, Shin-Ichi,Iizawa, Yuji,Baba, Masanori,Shiraishi, Mitsuru. "Orally active CCR5 antagonists as anti-HIV-1 agents: Synthesis and biological activity of 1-benzothiepine 1,1-dioxide and 1-benzazepine derivatives containing a tertiary amine moiety". . p. 577 - 590. Retrieved 2007/10/03.