2-(2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide

Base Information

• Chemical Name: 2-(2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide
• CAS No.: 1393900-70-3
• Molecular Formula: C₂₅H₂₇F₃N₆O
• Molecular Weight: 484.524
• Mol file: 1393900-70-3.mol

Synonyms:2-(2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide

Chemical Property of 2-(2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide

There total 16 articles about 2-(2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)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: 53.0%

tert-butyl 4-(4-((4-(2-(3-(2-amino-2-oxoethyl)pyridin-2-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (1393901-67-1) → 2-(2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide (1393900-70-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

Reference yield:

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (138647-49-1) → 2-(2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide (1393900-70-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium carbonate; lithium chloride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 4 h / 85 - 90 °C

2.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide; ethanol / 24 h / 20 °C

3.1: zinc(II) chloride / 1,2-dichloro-ethane; tert-butyl alcohol / 1 h / 0 °C / Inert atmosphere

3.2: 24.5 h / 0 - 20 °C

4.1: triethylamine / triphenylphosphine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.17 h / 120 °C / microwave irradiation

5.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide / 24 h / 20 °C

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

7.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

8.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; water; hydrogen; ammonium carbonate; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium chloride; zinc(II) chloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium 10% on activated carbon; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield:

2-(2-chloropyridin-3-yl)acetonitrile (101012-32-2) → 2-(2-(2-(2-((4-(piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide (1393900-70-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium hydroxide; water / 0.58 h / Reflux

1.2: 1 h / 0 °C / pH 1

2.1: acetyl chloride / 20 h / Reflux

3.1: triethylamine / triphenylphosphine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 20 h / 90 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.03 h / 0 °C

5.1: triethylamine / triphenylphosphine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.17 h / 120 °C / microwave irradiation

6.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide / 24 h / 20 °C

7.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 20 h / 20 °C

8.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

9.1: trifluoroacetic acid / dichloromethane / 24 h / 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; water; hydrogen; ammonium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; sodium hydroxide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; palladium 10% on activated carbon; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

2-(2-chloropyridin-3-yl)acetonitrile

tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate

2-Chloro-pyridin-3-yl acetic acid

Downstream raw materials:

2-(2-(2-(2-((4-(1-methylpiperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide

2-(2-(2-(2-((4-(1-ethylpiperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetamide

Refernces

• 1、 -. "FAK INHIBITORS". . . Retrieved 2012/09/10.