N-[5-{2-amino-3-[4-(aminosulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide

Base Information

• Chemical Name: N-[5-{2-amino-3-[4-(aminosulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide
• CAS No.: 1366127-89-0
• Molecular Formula: C₂₇H₂₁F₂N₅O₅S₂
• Molecular Weight: 597.623
• Mol file: 1366127-89-0.mol

Synonyms:N-[5-{2-amino-3-[4-(aminosulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide

Chemical Property of N-[5-{2-amino-3-[4-(aminosulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[5-{2-amino-3-[4-(aminosulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide

There total 7 articles about N-[5-{2-amino-3-[4-(aminosulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide 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: 38.0%

N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-2,4-difluorobenzenesulfonamide (1083326-73-1) + 4-(2-amino-6-chloro-3-quinolinyl)benzenesulfonamide (1366131-28-3) → N-[5-{2-amino-3-[4-(aminosulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (1366127-89-0)

Guidance literature:

With potassium phosphate; XPhos; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In water; butan-1-ol; at 100 ℃; for 16h; Inert atmosphere;

Reference yield:

6-chloroquinoline (612-57-7) → N-[5-{2-amino-3-[4-(aminosulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (1366127-89-0)

Guidance literature:

Multi-step reaction with 7 steps

1: N-Bromosuccinimide / acetic acid / 3.5 h / 70 - 115 °C

2: trifluoromethylsulfonic anhydride; urea hydrogen peroxide adduct / dichloromethane

3: trichlorophosphate / 1 h / Reflux

4: N-ethyl-N,N-diisopropylamine / butan-1-ol / 40 h / 130 °C / Sealed tube

5: trifluoroacetic acid / 3 h / 65 °C

6: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane; water / 3 h / 80 °C / Inert atmosphere

7: potassium phosphate; XPhos / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / water; butan-1-ol / 16 h / 100 °C / Inert atmosphere

With potassium phosphate; N-Bromosuccinimide; trifluoromethylsulfonic anhydride; potassium acetate; urea hydrogen peroxide adduct; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; XPhos; trichlorophosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,2-dimethoxyethane; dichloromethane; water; acetic acid; butan-1-ol; 6: Suzuki Coupling / 7: Suzuki Coupling;

Reference yield:

3-bromo-6-chloroquinoline (13669-65-3) → N-[5-{2-amino-3-[4-(aminosulfonyl)phenyl]-6-quinolinyl}-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (1366127-89-0)

Guidance literature:

Multi-step reaction with 6 steps

1: trifluoromethylsulfonic anhydride; urea hydrogen peroxide adduct / dichloromethane

2: trichlorophosphate / 1 h / Reflux

3: N-ethyl-N,N-diisopropylamine / butan-1-ol / 40 h / 130 °C / Sealed tube

4: trifluoroacetic acid / 3 h / 65 °C

5: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,2-dimethoxyethane; water / 3 h / 80 °C / Inert atmosphere

6: potassium phosphate; XPhos / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / water; butan-1-ol / 16 h / 100 °C / Inert atmosphere

With potassium phosphate; trifluoromethylsulfonic anhydride; potassium acetate; urea hydrogen peroxide adduct; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; XPhos; trichlorophosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,2-dimethoxyethane; dichloromethane; water; butan-1-ol; 5: Suzuki Coupling / 6: Suzuki Coupling;

upstream raw materials:

6-chloroquinoline

3-bromo-6-chloroquinoline

N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-2,4-difluorobenzenesulfonamide

4-(2-amino-6-chloro-3-quinolinyl)benzenesulfonamide