N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide

Base Information

• Chemical Name: N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide
• CAS No.: 1195768-39-8
• Molecular Formula: C₂₄H₁₈ClF₃N₄O₃S₂
• Molecular Weight: 567.012
• Mol file: 1195768-39-8.mol

Synonyms:N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide

Chemical Property of N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide

There total 13 articles about N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-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: 67.3%

3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluoroaniline (1195768-38-7) + 2,5-difluorobenzenesulfonyl chloride (26120-86-5) → N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide (1195768-39-8)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 18h;

Reference yield:

tetrahydro-pyran-4-carboxylic acid amide (344329-76-6) → N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide (1195768-39-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Lawessons reagent / tetrahydrofuran / 6 h / Reflux

2.1: N-Bromosuccinimide / N,N-dimethyl acetamide / 0 - 20 °C

2.2: 20 - 60 °C

3.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0 - 20 °C

4.1: pyridine / dichloromethane / 18 h / 20 °C

With Lawessons reagent; pyridine; N-Bromosuccinimide; tri-n-butyl-tin hydride; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide;

Reference yield:

2-fluoro-3-bromobenzoic acid methyl ester (206551-41-9) → N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide (1195768-39-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: caesium carbonate / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 90 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

3.1: sodium hydrogencarbonate / tetrahydrofuran / 0 - 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / -10 - 0 °C

4.2: 1.33 h / 0 - 20 °C

5.1: N-Bromosuccinimide / N,N-dimethyl acetamide / 0 - 20 °C

5.2: 20 - 60 °C

6.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0 - 20 °C

7.1: pyridine / dichloromethane / 18 h / 20 °C

With pyridine; N-Bromosuccinimide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; caesium carbonate; acetic acid; trifluoroacetic acid; lithium hexamethyldisilazane; bis-triphenylphosphine-palladium(II) chloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; toluene;

upstream raw materials:

3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluoroaniline

2,5-difluorobenzenesulfonyl chloride

tetrahydro-pyran-4-carboxylic acid amide

2-fluoro-3-bromobenzoic acid methyl ester

Refernces