1-(2-(2,4-dichlorobenzyl)-7-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-4-carbonitrile

Base Information

• Chemical Name: 1-(2-(2,4-dichlorobenzyl)-7-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-4-carbonitrile
• CAS No.: 1600524-65-9
• Molecular Formula: C₂₃H₂₁Cl₂N₇
• Molecular Weight: 466.373

Synonyms:1-(2-(2,4-dichlorobenzyl)-7-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-4-carbonitrile

Chemical Property of 1-(2-(2,4-dichlorobenzyl)-7-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-4-carbonitrile

Chemical Property:

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Technology Process of 1-(2-(2,4-dichlorobenzyl)-7-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-4-carbonitrile

There total 7 articles about 1-(2-(2,4-dichlorobenzyl)-7-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-4-carbonitrile 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: 89.0%

2,4-dichlorophenylacetic acid (19719-28-9) + 1-(3,4-diamino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)piperidine-4-carboxamide (1600524-54-6) → 1-(2-(2,4-dichlorobenzyl)-7-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-4-carbonitrile (1600524-65-9)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 180 ℃; for 0.166667h; Inert atmosphere; Sealed tube; Microwave irradiation;

DOI:10.1016/j.ejmech.2014.03.019

Reference yield:

2-chloro-4-amino-5-iodopyridine (800402-12-4) → 1-(2-(2,4-dichlorobenzyl)-7-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-4-carbonitrile (1600524-65-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sulfuric acid; nitric acid / 4 h / 20 °C / Cooling with ice

2: 1,4-dioxane; water / 6 h / 120 °C / Inert atmosphere; Sealed tube

3: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,2-dimethoxyethane / 3 h / 120 °C / Inert atmosphere; Schlenk technique; Sealed tube

4: palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 2 h / 20 °C / 2068.65 Torr / Inert atmosphere

5: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide / 0.17 h / 180 °C / Inert atmosphere; Sealed tube; Microwave irradiation

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sulfuric acid; palladium 10% on activated carbon; hydrogen; nitric acid; potassium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; 3: |Suzuki Coupling;

DOI:10.1016/j.ejmech.2014.03.019

Reference yield:

2-chloro-5-iodo-3-nitropyridin-4-amine (1600524-47-7) → 1-(2-(2,4-dichlorobenzyl)-7-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-4-carbonitrile (1600524-65-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,4-dioxane; water / 6 h / 120 °C / Inert atmosphere; Sealed tube

2: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,2-dimethoxyethane / 3 h / 120 °C / Inert atmosphere; Schlenk technique; Sealed tube

3: palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 2 h / 20 °C / 2068.65 Torr / Inert atmosphere

4: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / N,N-dimethyl-formamide / 0.17 h / 180 °C / Inert atmosphere; Sealed tube; Microwave irradiation

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; hydrogen; potassium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; 2: |Suzuki Coupling;

DOI:10.1016/j.ejmech.2014.03.019

upstream raw materials:

2-chloro-4-amino-5-iodopyridine

2-chloro-5-iodo-3-nitropyridin-4-amine

1-(4-amino-5-iodo-3-nitropyridin-2-yl)piperidine-4-carboxamide

1-(4-amino-5-(1-methyl-1H-pyrazol-4-yl)-3-nitropyridin-2-yl)piperidine-4-carboxamide

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