N-{4-[4-chloro-6-({3-[5-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl]-1H-pyrazol-4-yl}amino)pyrimidin-2-ylthio]phenyl}cyclopropanecarboxamide

Base Information

• Chemical Name: N-{4-[4-chloro-6-({3-[5-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl]-1H-pyrazol-4-yl}amino)pyrimidin-2-ylthio]phenyl}cyclopropanecarboxamide
• CAS No.: 1254229-30-5
• Molecular Formula: C₂₉H₂₈ClN₉O₂S
• Molecular Weight: 602.119
• Mol file: 1254229-30-5.mol

Synonyms:N-{4-[4-chloro-6-({3-[5-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl]-1H-pyrazol-4-yl}amino)pyrimidin-2-ylthio]phenyl}cyclopropanecarboxamide

Chemical Property of N-{4-[4-chloro-6-({3-[5-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl]-1H-pyrazol-4-yl}amino)pyrimidin-2-ylthio]phenyl}cyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{4-[4-chloro-6-({3-[5-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl]-1H-pyrazol-4-yl}amino)pyrimidin-2-ylthio]phenyl}cyclopropanecarboxamide

There total 7 articles about N-{4-[4-chloro-6-({3-[5-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl]-1H-pyrazol-4-yl}amino)pyrimidin-2-ylthio]phenyl}cyclopropanecarboxamide 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: 36.5%

3-(5-(morpholinylmethyl)-1H-benzo[d]imidazol-2-yl)-1H-pyrazole-4-amine (825619-30-5) + C14H12ClN3OS → N-{4-[4-chloro-6-({3-[5-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl]-1H-pyrazol-4-yl}amino)pyrimidin-2-ylthio]phenyl}cyclopropanecarboxamide (1254229-30-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; potassium iodide; In N,N-dimethyl-formamide; at 90 ℃; for 4h;

DOI:10.1016/j.bmcl.2013.04.039

Reference yield:

3,4-dinitrobenzoic acid (528-45-0) → N-{4-[4-chloro-6-({3-[5-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl]-1H-pyrazol-4-yl}amino)pyrimidin-2-ylthio]phenyl}cyclopropanecarboxamide (1254229-30-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 6 h / Reflux

2.1: triethylamine / tetrahydrofuran / 2 h / 0 - 5 °C

2.2: 10 - 20 °C

3.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.2: 0 °C / Reflux

4.1: 5%-palladium/activated carbon; hydrogen / ethanol / 48 h / 20 °C

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: 5%-palladium/activated carbon; hydrogen / ethanol / 48 h / 20 °C

7.1: potassium iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 90 °C

With sodium tetrahydroborate; thionyl chloride; 5%-palladium/activated carbon; boron trifluoride diethyl etherate; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; potassium iodide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2013.04.039

Reference yield:

4-(3,4-dinitrobenzyl)-morpholine (825619-03-2) → N-{4-[4-chloro-6-({3-[5-(morpholinomethyl)-1H-benzo[d]imidazol-2-yl]-1H-pyrazol-4-yl}amino)pyrimidin-2-ylthio]phenyl}cyclopropanecarboxamide (1254229-30-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 5%-palladium/activated carbon; hydrogen / ethanol / 48 h / 20 °C

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: 5%-palladium/activated carbon; hydrogen / ethanol / 48 h / 20 °C

4.1: potassium iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 90 °C

With 5%-palladium/activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium iodide; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2013.04.039

upstream raw materials:

4-(3,4-dinitrobenzyl)-morpholine

3,4-dinitrobenzoic acid

4-morpholin-4-ylmethylbenzene-1,2-diamine

4-((2-(4-nitro-1H-pyrazol-3-yl)-1H-benzo[d]imidazole-5-yl)methyl)morpholine