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

Base Information

Chemical Name:6-(2-(2-chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-isopropylpyridazin-3-amine
CAS No.:1542265-18-8
Molecular Formula:C₂₈H₃₀ClN₇
Molecular Weight:500.046
Hs Code.:

Synonyms:6-(2-(2-chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-isopropylpyridazin-3-amine

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

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

There total 9 articles about 6-(2-(2-chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-isopropylpyridazin-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: 65.0%

: 1542265-52-0
N-isopropyl-6-ethynylpyridazin-3-amine

: 1542265-53-1
2-(4-chloro-3-iodophenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazole

: 1542265-18-8
6-(2-(2-chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-isopropylpyridazin-3-amine

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:

: C₇H₁₀BrN₃

: 1542265-18-8
6-(2-(2-chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-isopropylpyridazin-3-amine

Guidance literature:: Multi-step reaction with 3 steps

1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / dichloromethane

3: 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⁾; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; 3: |Sonogashira Cross-Coupling;
DOI:10.1021/acs.jmedchem.1c00082

Reference yield:

: 528-45-0
3,4-dinitrobenzoic acid

: 1542265-18-8
6-(2-(2-chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-isopropylpyridazin-3-amine

Guidance literature:: Multi-step reaction with 6 steps

1.1: thionyl chloride / 6 h / Reflux

2.1: triethylamine / dichloromethane / 5 - 20 °C

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

3.2: 0.17 h

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

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 24 h / 20 °C

5.2: 3 h / Reflux

6.1: 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⁾; thionyl chloride; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 6.1: |Sonogashira Cross-Coupling;
DOI:10.1021/acs.jmedchem.1c00082