3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]-N-(pentylsulfonyl)propanamide

Base Information

• Chemical Name: 3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]-N-(pentylsulfonyl)propanamide
• CAS No.: 926378-02-1
• Molecular Formula: C₂₄H₂₈Cl₂N₄O₄S
• Molecular Weight: 539.483
• Mol file: 926378-02-1.mol

Synonyms:3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]-N-(pentylsulfonyl)propanamide

Chemical Property of 3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]-N-(pentylsulfonyl)propanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]-N-(pentylsulfonyl)propanamide

There total 11 articles about 3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]-N-(pentylsulfonyl)propanamide 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:

3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]propanoic acid (926296-20-0) + 1-pentylsulfonamide (52960-14-2) → 3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]-N-(pentylsulfonyl)propanamide (926378-02-1)

Guidance literature:

3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]propanoic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

1-pentylsulfonamide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 100 ℃; for 15h;

DOI:10.1016/j.bmc.2011.12.008

Reference yield:

methyl 2-(2,4-dichlorobenzyl)hydrazinecarboxylate (1357002-32-4) → 3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]-N-(pentylsulfonyl)propanamide (926378-02-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: methanol / 2 h / Reflux

1.2: 1 h / Reflux

2.1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 20 °C / Cooling with ice

3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0 - 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C

4.2: -78 - 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

5.2: 0 - 20 °C

6.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 6 h / 20 °C / 760.05 Torr

7.1: hydrogenchloride / ethanol; water / 6 h / Reflux

8.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C

9.1: sodium hydroxide / tetrahydrofuran; ethanol / 1 h / 50 °C

10.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 20 °C

10.2: 15 h / 100 °C

With hydrogenchloride; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,1'-carbonyldiimidazole; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Michael addition / 4.1: Swern oxidation / 4.2: Swern oxidation / 5.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.bmc.2011.12.008

Reference yield:

methyl 1-(2,4-dichlorobenzyl)-3-hydroxy-1H-pyrazole-5-carboxylate (888738-82-7) → 3-[1-(2,4-dichlorobenzyl)-3-(pyridin-2-ylmethoxy)-1H-pyrazol-5-yl]-N-(pentylsulfonyl)propanamide (926378-02-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 20 °C / Cooling with ice

2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0 - 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C

3.2: -78 - 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

4.2: 0 - 20 °C

5.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 6 h / 20 °C / 760.05 Torr

6.1: hydrogenchloride / ethanol; water / 6 h / Reflux

7.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C

8.1: sodium hydroxide / tetrahydrofuran; ethanol / 1 h / 50 °C

9.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 20 °C

9.2: 15 h / 100 °C

With hydrogenchloride; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,1'-carbonyldiimidazole; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.bmc.2011.12.008

upstream raw materials:

methyl 2-(2,4-dichlorobenzyl)hydrazinecarboxylate

methyl 1-(2,4-dichlorobenzyl)-3-hydroxy-1H-pyrazole-5-carboxylate

methyl 1-(2,4-dichlorobenzyl)-3-(methoxymethoxy)-1H-pyrazole-5-carboxylate

[1-(2,4-dichlorobenzyl)-3-(methoxymethoxy)-1H-pyrazol-5-yl]methanol

Refernces