3-(2-(2-(2-hydroxyethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

Base Information

• Chemical Name: 3-(2-(2-(2-hydroxyethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
• CAS No.: 1257628-67-3
• Molecular Formula: C₂₇H₂₃F₃N₆O₂
• Molecular Weight: 520.514
• Mol file: 1257628-67-3.mol

Synonyms:3-(2-(2-(2-hydroxyethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

Chemical Property of 3-(2-(2-(2-hydroxyethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-(2-(2-hydroxyethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

There total 4 articles about 3-(2-(2-(2-hydroxyethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide 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-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (1257628-83-3) + C6H8BrN3O (1187386-42-0) → 3-(2-(2-(2-hydroxyethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (1257628-67-3)

Guidance literature:

With copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine; In N,N-dimethyl-formamide; at 60 ℃; Sealed tube; Inert atmosphere;

DOI:10.1016/j.bmcl.2015.07.006

Reference yield:

3-iodo-4-toluic acid (82998-57-0) → 3-(2-(2-(2-hydroxyethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (1257628-67-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: thionyl chloride / N,N-dimethyl-formamide / 2 h / Reflux

2.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C

3.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere

3.2: 3 h / 20 °C

4.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere

With copper(l) iodide; thionyl chloride; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; palladium diacetate; triethylamine; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 3.1: |Sonogashira Cross-Coupling / 4.1: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmcl.2015.07.006

Reference yield:

3-iodo-4-methylbenzoyl chloride (52107-98-9) → 3-(2-(2-(2-hydroxyethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (1257628-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C

2.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere

2.2: 3 h / 20 °C

3.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere

With copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; palladium diacetate; triethylamine; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 2.1: |Sonogashira Cross-Coupling / 3.1: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmcl.2015.07.006

upstream raw materials:

3-iodo-4-toluic acid

3-iodo-4-methylbenzoyl chloride

3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

C₆H₈BrN₃O