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

Base Information

• Chemical Name: 3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluoroaniline
• CAS No.: 1195768-38-7
• Molecular Formula: C₁₈H₁₆ClFN₄OS
• Molecular Weight: 390.869
• Mol file: 1195768-38-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about 3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluoroaniline 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: 97.8%

2-propen-1-yl {3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluorophenyl}carbamate (1195768-37-6) → 3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluoroaniline (1195768-38-7)

Guidance literature:

With tri-n-butyl-tin hydride; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

Reference yield:

2-fluoro-3-nitrobenzoic acid methyl ester (946126-94-9) → 3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluoroaniline (1195768-38-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrazine hydrate / tetrahydrofuran; methanol / 70 °C / Inert atmosphere

2.1: sodium hydrogencarbonate / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 - 0 °C / Inert atmosphere

3.2: 1.33 h / 0 - 20 °C / Inert atmosphere

4.1: N-Bromosuccinimide / ISOPROPYLAMIDE / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 1.5 h / 20 - 60 °C / Inert atmosphere

5.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With N-Bromosuccinimide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; hydrazine hydrate; acetic acid; lithium hexamethyldisilazane; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; dichloromethane; ISOPROPYLAMIDE;

Reference yield:

2-fluoro-3-bromobenzoic acid methyl ester (206551-41-9) → 3-[5-(2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-4-yl]-2-fluoroaniline (1195768-38-7)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: 1 h / 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 - 0 °C / Inert atmosphere

3.2: 1.33 h / 0 - 20 °C / Inert atmosphere

4.1: N-Bromosuccinimide / ISOPROPYLAMIDE / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 1.5 h / 20 - 60 °C / Inert atmosphere

5.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

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

upstream raw materials:

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

3-bromo-2-fluorobenzoic acid

2-fluoro-3-nitrobenzoic acid methyl ester

2-fluoro-3-bromobenzoic acid methyl ester

Downstream raw materials:

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

Refernces

• 1、 -. "Benzene Sulfonamide Thiazole and Oxazole Compounds". Page/Page column 59. . Retrieved 2009/12/23.