4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile

Base Information

• Chemical Name: 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile
• CAS No.: 1616434-28-6
• Molecular Formula: C₃₀H₃₁ClN₆O
• Molecular Weight: 527.069
• Mol file: 1616434-28-6.mol

Synonyms:4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile

Chemical Property of 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile

There total 17 articles about 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-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: 88.0%

zinc(II) cyanide (557-21-1) + 6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine (1616434-27-5) → 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (1616434-28-6)

Guidance literature:

With sulfuric acid; palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; zinc; In N,N-dimethyl acetamide; at 100 ℃; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.jmedchem.1c01524

Reference yield:

2,6-dichloro-N3-((trans-4-methylcyclohexyl)methyl)pyridine-3,4-diamine (1658500-49-2) → 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (1616434-28-6)

Guidance literature:

Multi-step reaction with 5 steps

1: acetic anhydride / 3 h / 90 °C

2: N-Bromosuccinimide / chloroform / 1 h / Reflux

3: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 16 h / 100 °C / Sealed tube

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere; Sealed tube

5: (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; zinc; palladium diacetate; sulfuric acid / N,N-dimethyl acetamide / 3.5 h / 100 °C / Inert atmosphere; Sealed tube

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; N-Bromosuccinimide; sulfuric acid; palladium diacetate; acetic anhydride; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; zinc; In 1,4-dioxane; chloroform; N,N-dimethyl acetamide; dimethyl sulfoxide;

Reference yield:

4,6-dichloro-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine (1616434-24-2) → 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (1616434-28-6)

Guidance literature:

Multi-step reaction with 4 steps

1: N-Bromosuccinimide / chloroform / 1 h / Reflux

2: N-ethyl-N,N-diisopropylamine; potassium fluoride / dimethyl sulfoxide / 16 h / 100 °C / Sealed tube

3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere; Sealed tube

4: (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; zinc; palladium diacetate; sulfuric acid / N,N-dimethyl acetamide / 3.5 h / 100 °C / Inert atmosphere; Sealed tube

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; N-Bromosuccinimide; sulfuric acid; palladium diacetate; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; zinc; In 1,4-dioxane; chloroform; N,N-dimethyl acetamide; dimethyl sulfoxide;

upstream raw materials:

2,6-dichloro-3-nitropyridin-4-amine

tert-butyl (2,6-dichloro-3-nitropyridin-4-yl)carbamate

tert-butyl (2,6-dichloro-3-(((trans-4-methylcyclohexyl)methyl)amino)pyridin-4-yl)carbamate

2,6-dichloro-N³-((trans-4-methylcyclohexyl)methyl)pyridine-3,4-diamine

Downstream raw materials:

5-{4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,3,4-oxadiazol-2(3H)-one

methyl 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carboxylate

4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbohydrazide

4-(5-chloropyridin-3-yl)-N'-hydroxy-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carboximidamide