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

Base Information

• Chemical Name: 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
• CAS No.: 1616431-67-4
• Molecular Formula: C₃₁H₃₄ClN₅O₃
• Molecular Weight: 560.096
• Mol file: 1616431-67-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 17 articles about 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 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:

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) → 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 (1616431-67-4)

Guidance literature:

With hydrogenchloride; In methanol; at 75 ℃; for 3.5h;

Reference yield:

2,6-dichloro-3-nitropyridin-4-amine (2897-43-0) → 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 (1616431-67-4)

Guidance literature:

Multi-step reaction with 10 steps

1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -20 - 20 °C

2: iron; water / ethanol / 10 h / 20 °C

3: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 0 - 20 °C

4: hydrogenchloride / 1,4-dioxane / 15 h / 45 °C

5: acetic anhydride / 3 h / 90 °C

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

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

8: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere; Sealed tube

9: (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

10: hydrogenchloride / methanol / 3.5 h / 75 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; N-Bromosuccinimide; sulfuric acid; water; palladium diacetate; acetic anhydride; sodium tris(acetoxy)borohydride; iron; caesium carbonate; acetic acid; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl acetamide; dimethyl sulfoxide;

Reference yield:

tert-butyl (2,6-dichloro-3-nitropyridin-4-yl)carbamate (1313726-52-1) → 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 (1616431-67-4)

Guidance literature:

Multi-step reaction with 9 steps

1: iron; water / ethanol / 10 h / 20 °C

2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 0 - 20 °C

3: hydrogenchloride / 1,4-dioxane / 15 h / 45 °C

4: acetic anhydride / 3 h / 90 °C

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

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

7: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere; Sealed tube

8: (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

9: hydrogenchloride / methanol / 3.5 h / 75 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; N-Bromosuccinimide; sulfuric acid; water; palladium diacetate; acetic anhydride; sodium tris(acetoxy)borohydride; iron; caesium carbonate; acetic acid; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; zinc; In 1,4-dioxane; methanol; ethanol; dichloromethane; 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

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

Refernces