6-tert-butyl-N-((1R)-1-{3-methyl-4[(methylsulfonyl)amino]phenyl}-ethyl)quinoline-2-carboxamide

Base Information

• Chemical Name: 6-tert-butyl-N-((1R)-1-{3-methyl-4[(methylsulfonyl)amino]phenyl}-ethyl)quinoline-2-carboxamide
• CAS No.: 958328-02-4
• Molecular Formula: C₂₄H₂₉N₃O₃S
• Molecular Weight: 439.579
• Mol file: 958328-02-4.mol

Synonyms:6-tert-butyl-N-((1R)-1-{3-methyl-4[(methylsulfonyl)amino]phenyl}-ethyl)quinoline-2-carboxamide

Chemical Property of 6-tert-butyl-N-((1R)-1-{3-methyl-4[(methylsulfonyl)amino]phenyl}-ethyl)quinoline-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-tert-butyl-N-((1R)-1-{3-methyl-4[(methylsulfonyl)amino]phenyl}-ethyl)quinoline-2-carboxamide

There total 9 articles about 6-tert-butyl-N-((1R)-1-{3-methyl-4[(methylsulfonyl)amino]phenyl}-ethyl)quinoline-2-carboxamide 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: 35.0%

6-tert-butylquinoline-2-carboxylic acid + N-{4-[(1R)-1-aminoethyl]-2-methylphenyl}methanesulfonamide hydrochloride (886842-78-0) → 6-tert-butyl-N-((1R)-1-{3-methyl-4[(methylsulfonyl)amino]phenyl}-ethyl)quinoline-2-carboxamide (958328-02-4)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield:

4-hydroxy-3-methylphenyl methyl ketone (876-02-8) → 6-tert-butyl-N-((1R)-1-{3-methyl-4[(methylsulfonyl)amino]phenyl}-ethyl)quinoline-2-carboxamide (958328-02-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 16 h / 20 °C

2.1: caesium carbonate / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / 0.17 h / 120 °C / Microwave irradiation

3.1: tetrahydrofuran / 16 h / 70 °C / Inert atmosphere

4.1: sodium tetrahydroborate / tetrahydrofuran / 5 h / -70 °C / Inert atmosphere

4.2: 1 h / 20 °C / Inert atmosphere

5.1: hydrogenchloride / 1,4-dioxane; methanol / 0.5 h / 20 °C

6.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; caesium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

4-acetyl-2-methylphenyl trifluoromethanesulfonate (252561-07-2) → 6-tert-butyl-N-((1R)-1-{3-methyl-4[(methylsulfonyl)amino]phenyl}-ethyl)quinoline-2-carboxamide (958328-02-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: caesium carbonate / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / 0.17 h / 120 °C / Microwave irradiation

2.1: tetrahydrofuran / 16 h / 70 °C / Inert atmosphere

3.1: sodium tetrahydroborate / tetrahydrofuran / 5 h / -70 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride / 1,4-dioxane; methanol / 0.5 h / 20 °C

5.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; caesium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide;

upstream raw materials:

4-hydroxy-3-methylphenyl methyl ketone

4-acetyl-2-methylphenyl trifluoromethanesulfonate

N-{4-[(1R)-1-aminoethyl]-2-methylphenyl}methanesulfonamide hydrochloride

N-[4-((1R)-1-{[(R)-tert-butylsulfinyl]amino}ethyl)-2-methylphenyl]methanesulfonamide