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

Base Information

• Chemical Name: 2-(4-(2-(2-((4-(1-methylpiperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetamide
• CAS No.: 1393900-68-9
• Molecular Formula: C₂₅H₂₈F₃N₇O
• Molecular Weight: 499.539
• Mol file: 1393900-68-9.mol

Synonyms:

Chemical Property of 2-(4-(2-(2-((4-(1-methylpiperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-(2-(2-((4-(1-methylpiperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetamide

There total 15 articles about 2-(4-(2-(2-((4-(1-methylpiperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyrimidin-5-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:

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (138647-49-1) → 2-(4-(2-(2-((4-(1-methylpiperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetamide (1393900-68-9)

Guidance literature:

Multi-step reaction with 9 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 / copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate; trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 0.33 h / 120 °C / Inert atmosphere; microwave irradiation

5.1: hydrogen / palladium 10% on activated carbon / ethyl acetate; N,N-dimethyl-formamide / 22 h / 20 °C / Inert atmosphere

6.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 18 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; tetrahydrofuran / 44 h / 20 - 35 °C / Inert atmosphere

8.1: trifluoroacetic acid / dichloromethane / 23 h / 20 °C / Inert atmosphere

9.1: sodium tris(acetoxy)borohydride; methanol / water / 2.5 h / 20 °C / Inert atmosphere

With methanol; lithium hydroxide monohydrate; water; hydrogen; ammonium carbonate; sodium tris(acetoxy)borohydride; 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; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trans-bis(triphenylphosphine)palladium dichloride; palladium 10% on activated carbon; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield:

tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate (170011-57-1) → 2-(4-(2-(2-((4-(1-methylpiperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetamide (1393900-68-9)

Guidance literature:

Multi-step reaction with 7 steps

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

1.2: 24.5 h / 0 - 20 °C

2.1: triethylamine / copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate; trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 0.33 h / 120 °C / Inert atmosphere; microwave irradiation

3.1: hydrogen / palladium 10% on activated carbon / ethyl acetate; N,N-dimethyl-formamide / 22 h / 20 °C / Inert atmosphere

4.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 18 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium carbonate / N,N-dimethyl-formamide; tetrahydrofuran / 44 h / 20 - 35 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 23 h / 20 °C / Inert atmosphere

7.1: sodium tris(acetoxy)borohydride; methanol / water / 2.5 h / 20 °C / Inert atmosphere

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

Reference yield:

tert-butyl 4-(4-nitrophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (387827-33-0) → 2-(4-(2-(2-((4-(1-methylpiperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetamide (1393900-68-9)

Guidance literature:

Multi-step reaction with 8 steps

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

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

2.2: 24.5 h / 0 - 20 °C

3.1: triethylamine / copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate; trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 0.33 h / 120 °C / Inert atmosphere; microwave irradiation

4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate; N,N-dimethyl-formamide / 22 h / 20 °C / Inert atmosphere

5.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 18 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; ammonium carbonate / N,N-dimethyl-formamide; tetrahydrofuran / 44 h / 20 - 35 °C / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 23 h / 20 °C / Inert atmosphere

8.1: sodium tris(acetoxy)borohydride; methanol / water / 2.5 h / 20 °C / Inert atmosphere

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

upstream raw materials:

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

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

tert-butyl 4-(4-nitrophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate

diethyl 2-formylbutanedioate

Refernces

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