1H-BenziMidazole, 6-(4-MorpholinylMethyl)-2-(4-nitro-1H-pyrazol-3-yl)-

Base Information

• Chemical Name: 1H-BenziMidazole, 6-(4-MorpholinylMethyl)-2-(4-nitro-1H-pyrazol-3-yl)-
• CAS No.: 825619-29-2
• Molecular Formula: C15H16N6O3
• Molecular Weight: 328.32600
• Mol file: 825619-29-2.mol

Synonyms:

Chemical Property of 1H-BenziMidazole, 6-(4-MorpholinylMethyl)-2-(4-nitro-1H-pyrazol-3-yl)-

Chemical Property:

• PSA: 115.65000
• LogP: 2.15450

Purity/Quality:

NLT 98% ^*data from raw suppliers

1H-Benzimidazole,6-(4-morpholinylmethyl)-2-(4-nitro-1H-pyrazol-3-yl)- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-BenziMidazole, 6-(4-MorpholinylMethyl)-2-(4-nitro-1H-pyrazol-3-yl)-

There total 6 articles about 1H-BenziMidazole, 6-(4-MorpholinylMethyl)-2-(4-nitro-1H-pyrazol-3-yl)- 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: 61.0%

4-morpholin-4-ylmethylbenzene-1,2-diamine (825619-02-1) + 4-nitro-1H-pyrazole-3-carboxylic acid (5334-40-7) → 4-((2-(4-nitro-1H-pyrazol-3-yl)-1H-benzo[d]imidazole-5-yl)methyl)morpholine (825619-29-2)

Guidance literature:

4-morpholin-4-ylmethylbenzene-1,2-diamine; 4-nitro-1H-pyrazole-3-carboxylic acid; With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

With acetic acid; for 3h; Product distribution / selectivity; Heating / reflux;

Reference yield:

4-(3,4-dinitrobenzyl)-morpholine (825619-03-2) → 4-((2-(4-nitro-1H-pyrazol-3-yl)-1H-benzo[d]imidazole-5-yl)methyl)morpholine (825619-29-2)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1016/j.bmcl.2013.04.039

Reference yield:

3,4-dinitrobenzoic acid (528-45-0) → 4-((2-(4-nitro-1H-pyrazol-3-yl)-1H-benzo[d]imidazole-5-yl)methyl)morpholine (825619-29-2)

Guidance literature:

Multi-step reaction with 5 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

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,N-dimethyl-formamide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2013.04.039

upstream raw materials:

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

4-nitro-1H-pyrazole-3-carboxylic acid

4-(3,4-dinitrobenzyl)-morpholine

3,4-dinitrobenzoic acid

Downstream raw materials:

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