2-(4-((3'-amino[3,6'-biquinolin]-4'-yl)amino)phenyl)-2-methyl propanenitrile

Base Information

• Chemical Name: 2-(4-((3'-amino[3,6'-biquinolin]-4'-yl)amino)phenyl)-2-methyl propanenitrile
• CAS No.: 1201646-92-5
• Molecular Formula: C₂₈H₂₃N₅
• Molecular Weight: 429.524
• Mol file: 1201646-92-5.mol

Synonyms:2-(4-((3'-amino[3,6'-biquinolin]-4'-yl)amino)phenyl)-2-methyl propanenitrile

Chemical Property of 2-(4-((3'-amino[3,6'-biquinolin]-4'-yl)amino)phenyl)-2-methyl propanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-((3'-amino[3,6'-biquinolin]-4'-yl)amino)phenyl)-2-methyl propanenitrile

There total 17 articles about 2-(4-((3'-amino[3,6'-biquinolin]-4'-yl)amino)phenyl)-2-methyl propanenitrile 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: 47.0%

2-methyl-2-(4-((3'-nitro[3,6-biquinolin]-4'-yl)amino)-phenyl)propanenitrile (1201646-91-4) → 2-(4-((3'-amino[3,6'-biquinolin]-4'-yl)amino)phenyl)-2-methyl propanenitrile (1201646-92-5)

Guidance literature:

With hydrogen; Ra-Ni; In tetrahydrofuran; methanol; for 3h; under 1551.49 Torr;

Reference yield: 2.0%

2-(4-((3-amino-6-iodoquinolin-4-yl)amino)phenyl)-2-methylpropanenitrile (1628077-36-0) + quinolin-3-ylboronic acid (191162-39-7) → 2-(4-((3'-amino[3,6'-biquinolin]-4'-yl)amino)phenyl)-2-methyl propanenitrile (1201646-92-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 175 ℃; for 0.25h; Inert atmosphere; Sealed tube; Microwave irradiation;

DOI:10.1021/jm500361r

Reference yield:

6-bromo-3-nitroquinolin-4-ol (853908-50-6) → 2-(4-((3'-amino[3,6'-biquinolin]-4'-yl)amino)phenyl)-2-methyl propanenitrile (1201646-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: trichlorophosphate; N,N-dimethyl-formamide / 4 h / Reflux

2: sodium acetate; acetic acid / 0.5 h / 20 °C

3: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 8 h / 100 °C / Inert atmosphere

4: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; sodium acetate; potassium carbonate; acetic acid; N,N-dimethyl-formamide; trichlorophosphate; In 1,4-dioxane; methanol; water; 3: |Suzuki Coupling;

DOI:10.1039/c5md00401b

upstream raw materials:

2-methyl-2-(4-((3'-nitro[3,6-biquinolin]-4'-yl)amino)-phenyl)propanenitrile

6-iodo-3-nitroquinolin-4-ol

5-iodo-2-((2-nitrovinyl)amino)benzoic acid

2-(4-((6-iodo-3-nitroquinolin-4-yl)amino)phenyl)-2-methylpropanenitrile

Downstream raw materials:

C₂₉H₂₁N₅

C₃₀H₂₁N₅O₂

Refernces

• 1、 Seixas, Jo?o D.,Luengo-Arratta, Sandra A.,Diaz, Rosario,Saldivia, Manuel,Rojas-Barros, Domingo I.,Manzano, Pilar,Gonzalez, Silvia,Berlanga, Manuela,Smith, Terry K.,Navarro, Miguel,Pollastri, Michael P.. "Establishment of a structure-activity relationship of 1 H-imidazo[4,5-c]quinoline-based kinase inhibitor NVP-BEZ235 as a lead for African sleeping sickness". . p. 4834 - 4848. Retrieved 2014/07/07.