N-{3-[2-(1-amino-1-methylethyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide

Base Information

• Chemical Name: N-{3-[2-(1-amino-1-methylethyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide
• CAS No.: 1195767-93-1
• Molecular Formula: C₂₁H₂₀FN₅O₃S₂
• Molecular Weight: 473.552
• Mol file: 1195767-93-1.mol

Synonyms:N-{3-[2-(1-amino-1-methylethyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide

Chemical Property of N-{3-[2-(1-amino-1-methylethyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{3-[2-(1-amino-1-methylethyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide

There total 12 articles about N-{3-[2-(1-amino-1-methylethyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide 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: 24.0%

1,1-dimethylethyl [1-(5-(2-chloro-4-pyrimidinyl)-4-{2-fluoro-3-[(3-furanylsulfonyl)amino]phenyl}-1,3-thiazol-2-yl)-1-methylethyl]carbamate (1195769-61-9) + dimethyl zinc(II) (544-97-8) → N-{3-[2-(1-amino-1-methylethyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide (1195767-93-1)

Guidance literature:

1,1-dimethylethyl [1-(5-(2-chloro-4-pyrimidinyl)-4-{2-fluoro-3-[(3-furanylsulfonyl)amino]phenyl}-1,3-thiazol-2-yl)-1-methylethyl]carbamate; dimethyl zinc(II); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 80 ℃; for 3h; Inert atmosphere;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

Reference yield:

2-fluoro-3-bromobenzoic acid methyl ester (206551-41-9) → N-{3-[2-(1-amino-1-methylethyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide (1195767-93-1)

Guidance literature:

Multi-step reaction with 8 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 / dichloromethane

5.2: 2 h / 80 °C

6.1: water; tri-n-butyl-tin hydride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane

7.1: pyridine / dichloromethane / 20 °C

8.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

8.2: 0.5 h / 20 °C

With pyridine; N-Bromosuccinimide; water; tri-n-butyl-tin hydride; sodium hydrogencarbonate; caesium carbonate; trifluoroacetic acid; lithium hexamethyldisilazane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; dichloromethane; toluene;

Reference yield:

2-fluoro-3-nitrobenzoic acid methyl ester (946126-94-9) → N-{3-[2-(1-amino-1-methylethyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-3-furansulfonamide (1195767-93-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hydrazine hydrate / nickel / tetrahydrofuran; methanol; water / 70 °C

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

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

3.2: 1.33 h / 0 - 20 °C

4.1: N-Bromosuccinimide / dichloromethane

4.2: 2 h / 80 °C

5.1: water; tri-n-butyl-tin hydride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane

6.1: pyridine / dichloromethane / 20 °C

7.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

7.2: 0.5 h / 20 °C

With pyridine; N-Bromosuccinimide; water; tri-n-butyl-tin hydride; sodium hydrogencarbonate; hydrazine hydrate; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

upstream raw materials:

1,1-dimethylethyl [1-(5-(2-chloro-4-pyrimidinyl)-4-{2-fluoro-3-[(3-furanylsulfonyl)amino]phenyl}-1,3-thiazol-2-yl)-1-methylethyl]carbamate

dimethyl zinc(II)

2-fluoro-3-bromobenzoic acid methyl ester

2-fluoro-3-nitrobenzoic acid methyl ester