3-(2-amino-7-fluoro-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)propanamide

Base Information

• Chemical Name: 3-(2-amino-7-fluoro-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)propanamide
• CAS No.: 1309364-62-2
• Molecular Formula: C₂₆H₃₀FN₃O
• Molecular Weight: 419.542
• Mol file: 1309364-62-2.mol

Synonyms:3-(2-amino-7-fluoro-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)propanamide

Chemical Property of 3-(2-amino-7-fluoro-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)propanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-amino-7-fluoro-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)propanamide

There total 9 articles about 3-(2-amino-7-fluoro-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)propanamide 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:

N-(cyclohexylmethyl)-3-(7-fluoro-2-(4-methoxybenzylamino)-6-o-tolylquinolin-3-yl)propanamide (1309365-76-1) → 3-(2-amino-7-fluoro-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)propanamide (1309364-62-2)

Guidance literature:

With trifluoroacetic acid; for 3h; Reflux;

Reference yield:

N-(4-bromo-3-fluorophenyl)ethanamide (351-30-4) → 3-(2-amino-7-fluoro-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)propanamide (1309364-62-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: trichlorophosphate / 48.5 h / 75 °C / Inert atmosphere; Sealed tube; Cooling with ice

2.1: ethanol / 2.5 h / 125 °C / Sealed tube

3.1: tetrahydrofuran / 2.5 h / 70 °C

4.1: water; lithium hydroxide / tetrahydrofuran; methanol / 0.75 h / 20 °C

4.2: pH ~ 1

5.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / 1-methyl-pyrrolidin-2-one / 1 h

6.1: hydrogen / platinum on carbon / ethanol / 18 h

7.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 85 °C

8.1: potassium acetate / bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II) / ethanol; water / 5 h / Reflux

9.1: trifluoroacetic acid / 3 h / Reflux

With water; hydrogen; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; trichlorophosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); platinum on carbon; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; ethanol; water;

Reference yield:

6-bromo-7-fluoro-2-(4-methoxybenzylamino)quinoline-3-carbaldehyde (1309365-71-6) → 3-(2-amino-7-fluoro-6-o-tolylquinolin-3-yl)-N-(cyclohexylmethyl)propanamide (1309364-62-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: tetrahydrofuran / 2.5 h / 70 °C

2.1: water; lithium hydroxide / tetrahydrofuran; methanol / 0.75 h / 20 °C

2.2: pH ~ 1

3.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / 1-methyl-pyrrolidin-2-one / 1 h

4.1: hydrogen / platinum on carbon / ethanol / 18 h

5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 85 °C

6.1: potassium acetate / bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II) / ethanol; water / 5 h / Reflux

7.1: trifluoroacetic acid / 3 h / Reflux

With water; hydrogen; potassium acetate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); platinum on carbon; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; ethanol; water;

upstream raw materials:

N-(4-bromo-3-fluorophenyl)ethanamide

6-bromo-2-chloro-7-fluoroquinoline-3-carbaldehyde

6-bromo-7-fluoro-2-(4-methoxybenzylamino)quinoline-3-carbaldehyde

(E)-methyl 3-(6-bromo-7-fluoro-2-(4-methoxybenzylamino)quinolin-3-yl)acrylate

Refernces