N-isopropyl-6-(2-(2-methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)pyridazin-3-amine

Base Information

• Chemical Name: N-isopropyl-6-(2-(2-methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)pyridazin-3-amine
• CAS No.: 1542265-13-3
• Molecular Formula: C₂₉H₃₃N₇
• Molecular Weight: 479.628
• Mol file: 1542265-13-3.mol

Synonyms:

Chemical Property of N-isopropyl-6-(2-(2-methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)pyridazin-3-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-isopropyl-6-(2-(2-methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)pyridazin-3-amine

There total 8 articles about N-isopropyl-6-(2-(2-methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)pyridazin-3-amine 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: 37.0%

2-(3-iodo-4-methylphenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazole (1542265-50-8) + N-isopropyl-6-ethynylpyridazin-3-amine (1542265-52-0) → N-isopropyl-6-(2-(2-methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)pyridazin-3-amine (1542265-13-3)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c00082

Reference yield:

(3,4-dinitrophenyl)-(4-methylpiperazin-1-yl)-methanone (896466-69-6) → N-isopropyl-6-(2-(2-methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)pyridazin-3-amine (1542265-13-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 5 - 20 °C

1.2: 0.17 h

2.1: hydrogen; palladium 10% on activated carbon / methanol; N,N-dimethyl-formamide / 12 h

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C

3.2: 3 h / Reflux

4.1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 4.1: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.1c00082

Reference yield:

1-(3,4-dinitrobenzyl)-4-methylpiperazine (896466-70-9) → N-isopropyl-6-(2-(2-methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)pyridazin-3-amine (1542265-13-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen; palladium 10% on activated carbon / methanol; N,N-dimethyl-formamide / 12 h

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C

2.2: 3 h / Reflux

3.1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; 3.1: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.1c00082

upstream raw materials:

3,4-dinitrobenzoic acid

(3,4-dinitrophenyl)-(4-methylpiperazin-1-yl)-methanone

1-(3,4-dinitrobenzyl)-4-methylpiperazine

4-((4-methylpiperazin-1-yl)methyl)benzene-1,2-diamine