5-amino-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-phenyl-1H-pyrazole-4-carboxamide

Base Information

• Chemical Name: 5-amino-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-phenyl-1H-pyrazole-4-carboxamide
• CAS No.: 796069-77-7
• Molecular Formula: C₂₁H₂₁N₅O₂
• Molecular Weight: 375.43
• Mol file: 796069-77-7.mol

Synonyms:

Chemical Property of 5-amino-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-phenyl-1H-pyrazole-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-amino-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-phenyl-1H-pyrazole-4-carboxamide

There total 8 articles about 5-amino-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-phenyl-1H-pyrazole-4-carboxamide 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: 78.0%

3-(5-amino-1-phenyl-1H-pyrazole-4-carboxamido)-4-methylbenzoic acid + Cyclopropylamine (765-30-0) → 5-amino-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-phenyl-1H-pyrazole-4-carboxamide (796069-77-7)

Guidance literature:

3-(5-amino-1-phenyl-1H-pyrazole-4-carboxamido)-4-methylbenzoic acid; With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; for 1h;

Cyclopropylamine; In N,N-dimethyl-formamide; for 20h;

DOI:10.1021/acs.jmedchem.9b01227

Reference yield:

ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate (16078-71-0) → 5-amino-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-phenyl-1H-pyrazole-4-carboxamide (796069-77-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / water; methanol / 3 h / 80 °C

3.1: thionyl chloride / 1 h / Inert atmosphere

4.1: pyridine / dichloromethane / 1 h / 20 °C

5.1: palladium 10% on activated carbon; hydrogen / methanol / 40 °C

6.1: lithium hydroxide monohydrate / methanol; water / 48 h / 20 °C

7.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h

7.2: 20 h

With pyridine; thionyl chloride; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; sodium hydride; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 4.1: |Schotten-Baumann Reaction;

DOI:10.1021/acs.jmedchem.9b01227

Reference yield:

ethyl 5-(dibenzylamino)-1-phenyl-1H-pyrazole-4-carboxylate → 5-amino-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)-1-phenyl-1H-pyrazole-4-carboxamide (796069-77-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium hydroxide monohydrate / water; methanol / 3 h / 80 °C

2.1: thionyl chloride / 1 h / Inert atmosphere

3.1: pyridine / dichloromethane / 1 h / 20 °C

4.1: palladium 10% on activated carbon; hydrogen / methanol / 40 °C

5.1: lithium hydroxide monohydrate / methanol; water / 48 h / 20 °C

6.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h

6.2: 20 h

With pyridine; thionyl chloride; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 3.1: |Schotten-Baumann Reaction;

DOI:10.1021/acs.jmedchem.9b01227

upstream raw materials:

Cyclopropylamine

ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate

phenylhydrazine