3-(4-(5-chloropyridin-3-yl)-2-(cyclopropyl(ethoxy)methyl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one

Base Information

• Chemical Name: 3-(4-(5-chloropyridin-3-yl)-2-(cyclopropyl(ethoxy)methyl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one
• CAS No.: 1616430-95-5
• Molecular Formula: C₂₇H₃₁ClN₆O₃
• Molecular Weight: 523.035
• Mol file: 1616430-95-5.mol

Synonyms:3-(4-(5-chloropyridin-3-yl)-2-(cyclopropyl(ethoxy)methyl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one

Chemical Property of 3-(4-(5-chloropyridin-3-yl)-2-(cyclopropyl(ethoxy)methyl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-(5-chloropyridin-3-yl)-2-(cyclopropyl(ethoxy)methyl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one

There total 13 articles about 3-(4-(5-chloropyridin-3-yl)-2-(cyclopropyl(ethoxy)methyl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one 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: 82.0%

C26H33ClN6O2 + 1,1'-carbonyldiimidazole (530-62-1) → 3-(4-(5-chloropyridin-3-yl)-2-(cyclopropyl(ethoxy)methyl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one (1616430-95-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/acs.jmedchem.1c01524

Reference yield:

trans-4-methylcyclohexanecarboxylic acid (934-67-8,4331-54-8,13064-83-0) → 3-(4-(5-chloropyridin-3-yl)-2-(cyclopropyl(ethoxy)methyl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one (1616430-95-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: thionyl chloride / tetrahydrofuran / 2 h / 20 - 50 °C / Inert atmosphere

1.2: 1 h / 0 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere; Reflux

3.1: chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane / tetrahydrofuran / 20 °C / Inert atmosphere

4.1: acetic anhydride; hydrogenchloride / 1,4-dioxane / 2 h / 90 °C

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

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

7.1: LiMgTMPCl₂ / tetrahydrofuran; toluene / 0.75 h / -78 °C / Inert atmosphere

7.2: 2 h / -78 °C / Inert atmosphere

8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 - 20 °C / Inert atmosphere

8.2: 0 - 20 °C / Inert atmosphere

9.1: sodium hydrogencarbonate; hydroxylamine hydrochloride / water; ethanol / 1 h / 100 °C

10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 20 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium aluminium tetrahydride; thionyl chloride; chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sulfuric acid; hydroxylamine hydrochloride; palladium diacetate; acetic anhydride; sodium hydride; sodium hydrogencarbonate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl acetamide; water; toluene; acetonitrile; mineral oil; 5.1: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.1c01524

Reference yield:

2,6-dichloro-[4]pyridylamine (2587-02-2) → 3-(4-(5-chloropyridin-3-yl)-2-(cyclopropyl(ethoxy)methyl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridin-6-yl)-1,2,4-oxadiazol-5(4H)-one (1616430-95-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: acetic acid; potassium acetate / 30 °C / Inert atmosphere

1.2: 25 - 40 °C / Inert atmosphere

2.1: chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane / tetrahydrofuran / 20 °C / Inert atmosphere

3.1: acetic anhydride; hydrogenchloride / 1,4-dioxane / 2 h / 90 °C

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

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

6.1: LiMgTMPCl₂ / tetrahydrofuran; toluene / 0.75 h / -78 °C / Inert atmosphere

6.2: 2 h / -78 °C / Inert atmosphere

7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 - 20 °C / Inert atmosphere

7.2: 0 - 20 °C / Inert atmosphere

8.1: sodium hydrogencarbonate; hydroxylamine hydrochloride / water; ethanol / 1 h / 100 °C

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1 h / 20 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sulfuric acid; hydroxylamine hydrochloride; potassium acetate; palladium diacetate; acetic anhydride; sodium hydride; sodium hydrogencarbonate; caesium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl acetamide; water; toluene; acetonitrile; mineral oil; 4.1: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.1c01524

upstream raw materials:

trans-4-methylcyclohexanecarboxylic acid

2,6-dichloro-[4]pyridylamine

1,1'-carbonyldiimidazole

6-chloro-4-(5-chloropyridin-3-yl)-3-(((trans)-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine

Refernces

• 1、 -. "Substituted Imidazopyridines as HDM2 Inhibitors". Paragraph 0974. . Retrieved 2014/07/08.