N-(1-((5-cyanopyridin-2-yl)methyl)-1H-pyrazol-3-yl)-2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetamide

Base Information

• Chemical Name: N-(1-((5-cyanopyridin-2-yl)methyl)-1H-pyrazol-3-yl)-2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetamide
• CAS No.: 1838651-58-3
• Molecular Formula: C₂₂H₁₈F₃N₅O
• Molecular Weight: 425.413
• Mol file: 1838651-58-3.mol

Synonyms:

Chemical Property of N-(1-((5-cyanopyridin-2-yl)methyl)-1H-pyrazol-3-yl)-2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetamide

Chemical Property:

• Boiling Point: 646.4±55.0 °C(Predicted)
• Density: 1.36±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

ACT-709478 99.68% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(1-((5-cyanopyridin-2-yl)methyl)-1H-pyrazol-3-yl)-2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetamide

There total 6 articles about N-(1-((5-cyanopyridin-2-yl)methyl)-1H-pyrazol-3-yl)-2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetamide 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: 58.0%

2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetic acid + 6-((3-amino-1H-pyrazol-1-yl)methyl)nicotinonitrile → N-(1-((5-cyanopyridin-2-yl)methyl)-1H-pyrazol-3-yl)-2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetamide (1838651-58-3)

Guidance literature:

2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetic acid; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In acetonitrile; at 20 ℃; for 0.0833333h; Inert atmosphere;

6-((3-amino-1H-pyrazol-1-yl)methyl)nicotinonitrile; In acetonitrile; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01236

Reference yield:

6-((3-nitro-1H-pyrazol-1-yl)methyl)nicotinonitrile → N-(1-((5-cyanopyridin-2-yl)methyl)-1H-pyrazol-3-yl)-2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetamide (1838651-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ammonium chloride; iron / ethanol; water / 1.5 h / 75 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / acetonitrile / 0.08 h / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With iron; ammonium chloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In ethanol; water; acetonitrile;

DOI:10.1021/acs.jmedchem.7b01236

Reference yield:

1-bromo-4-(1-(trifluoromethyl)cycloprop-1-yl)benzene (1227160-18-0) → N-(1-((5-cyanopyridin-2-yl)methyl)-1H-pyrazol-3-yl)-2-(4-(1-(trifluoromethyl)cyclopropyl)phenyl)acetamide (1838651-58-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / tetrahydrofuran; diethyl ether / 90 °C / Inert atmosphere

2.1: formic acid / 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / acetonitrile / 0.08 h / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; formic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; XPhos; In tetrahydrofuran; diethyl ether; acetonitrile; 1.1: |Negishi Coupling;

DOI:10.1021/acs.jmedchem.7b01236

upstream raw materials:

1-bromo-4-(1-(trifluoromethyl)cycloprop-1-yl)benzene

2-bromomethyl-5-cyanopyridine