4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(4-hydroxycyclohexyl)-2-piperazinone

Base Information

• Chemical Name: 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(4-hydroxycyclohexyl)-2-piperazinone
• CAS No.: 1297137-70-2
• Molecular Formula: C₂₂H₂₄ClF₃N₄O₃
• Molecular Weight: 484.906
• Mol file: 1297137-70-2.mol

Synonyms:

Chemical Property of 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(4-hydroxycyclohexyl)-2-piperazinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(4-hydroxycyclohexyl)-2-piperazinone

There total 14 articles about 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(4-hydroxycyclohexyl)-2-piperazinone 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-hydroxy-2-trifluoromethylpyridine (170886-13-2) → 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(4-hydroxycyclohexyl)-2-piperazinone (1297137-70-2) + 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(trans-4-hydroxycyclohexyl)-2-piperazinone

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 °C

1.2: 3 h / 5 - 20 °C

2.1: dichloromethane / 20 °C

2.2: Cooling

3.1: potassium carbonate / N,N-dimethyl-formamide / 5 - 20 °C

4.1: sulfuric acid / 2 h / 90 °C

4.2: 90 °C

5.1: sulfuric acid / Reflux

5.2: 90 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C

7.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere

8.1: 3-(1-{[3,4-dichloro-5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-yl]carbonyl}-4-piperidinyl)-1,3-oxazolidin-2-one / N,N-dimethyl-formamide / 1 h / 60 °C

9.1: sodium hydroxide / methanol / 4 h / 50 °C

10.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C

10.2: 1.5 h / 0 °C

10.3: 0.75 h

With potassium phosphate; sulfuric acid; 3-(1-{[3,4-dichloro-5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-yl]carbonyl}-4-piperidinyl)-1,3-oxazolidin-2-one; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sulfuric acid; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

dimethyl 5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate (1297136-80-1) → 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(4-hydroxycyclohexyl)-2-piperazinone (1297137-70-2) + 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(trans-4-hydroxycyclohexyl)-2-piperazinone

Guidance literature:

Multi-step reaction with 8 steps

1.1: water; sulfuric acid / 40 h / 90 °C

2.1: ethanethiol; aluminum tri-bromide / 48 h / 20 °C

3.1: sulfuric acid / Reflux

3.2: 90 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C

5.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere

6.1: 3-(1-{[3,4-dichloro-5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-yl]carbonyl}-4-piperidinyl)-1,3-oxazolidin-2-one / N,N-dimethyl-formamide / 1 h / 60 °C

7.1: sodium hydroxide / methanol / 4 h / 50 °C

8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C

8.2: 1.5 h / 0 °C

8.3: 0.75 h

With potassium phosphate; aluminum tri-bromide; sulfuric acid; 3-(1-{[3,4-dichloro-5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-yl]carbonyl}-4-piperidinyl)-1,3-oxazolidin-2-one; water; N-ethyl-N,N-diisopropylamine; ethanethiol; sodium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sulfuric acid; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

1-amino-4-(ethyloxy)-2-(triftuoromethyl)pyridinium 2,4,6-trimethylbenzenesulfonate (1297137-84-8) → 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(4-hydroxycyclohexyl)-2-piperazinone (1297137-70-2) + 4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-(trans-4-hydroxycyclohexyl)-2-piperazinone

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 5 - 20 °C

2.1: sulfuric acid / 2 h / 90 °C

2.2: 90 °C

3.1: sulfuric acid / Reflux

3.2: 90 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C

5.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere

6.1: 3-(1-{[3,4-dichloro-5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-yl]carbonyl}-4-piperidinyl)-1,3-oxazolidin-2-one / N,N-dimethyl-formamide / 1 h / 60 °C

7.1: sodium hydroxide / methanol / 4 h / 50 °C

8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C

8.2: 1.5 h / 0 °C

8.3: 0.75 h

With potassium phosphate; sulfuric acid; 3-(1-{[3,4-dichloro-5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-yl]carbonyl}-4-piperidinyl)-1,3-oxazolidin-2-one; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sulfuric acid; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

4-hydroxy-2-trifluoromethylpyridine

methyl 3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylate

dimethyl 5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2,3-dicarboxylate

5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid

Refernces