N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylthio)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methane sulfonamide

Base Information

• Chemical Name: N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylthio)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methane sulfonamide
• CAS No.: 1353576-49-4
• Molecular Formula: C₁₈H₁₆ClFN₄O₃S₂
• Molecular Weight: 454.933
• Mol file: 1353576-49-4.mol

Synonyms:N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylthio)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methane sulfonamide

Chemical Property of N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylthio)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methane sulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylthio)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methane sulfonamide

There total 8 articles about N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylthio)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methane sulfonamide 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:

2-bromo-4-chloro-1-fluorobenzene (1996-30-1) → N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylthio)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methane sulfonamide (1353576-49-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / hexane; tetrahydrofuran / 0.83 h / -75 - -65 °C

1.2: 1.25 h / -70 - -65 °C

1.3: -60 - -10 °C / pH 1 - 2

2.1: potassium permanganate / water; tert-butyl alcohol / 2.92 h / 30 - 65 °C

2.2: 0.17 h / 20 °C

2.3: 15 - 25 °C / pH 1

3.1: sulfuric acid / Reflux

4.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 19 h / 0 - 20 °C

5.2: 1 h / 20 °C

6.1: N-Bromosuccinimide / dichloromethane / 2.25 h / -5 - 20 °C

6.2: 20 °C

7.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.17 h / 135 °C

8.1: sulfuric acid / ethanol / 20 °C / Reflux

9.1: pyridine / dichloromethane / 20 °C

9.2: 20 °C

9.3: 2 h / 60 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium permanganate; N-Bromosuccinimide; n-butyllithium; sulfuric acid; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; water; tert-butyl alcohol;

Reference yield:

3-bromo-5-chloro-2-fluorobenzoic acid (1269232-93-0) → N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylthio)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methane sulfonamide (1353576-49-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid / Reflux

2.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 19 h / 0 - 20 °C

3.2: 1 h / 20 °C

4.1: N-Bromosuccinimide / dichloromethane / 2.25 h / -5 - 20 °C

4.2: 20 °C

5.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.17 h / 135 °C

6.1: sulfuric acid / ethanol / 20 °C / Reflux

7.1: pyridine / dichloromethane / 20 °C

7.2: 20 °C

7.3: 2 h / 60 °C

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-Bromosuccinimide; sulfuric acid; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane;

Reference yield:

methyl 3-bromo-5-chloro-2-fluorobenzoate (1353575-32-2) → N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylthio)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methane sulfonamide (1353576-49-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 19 h / 0 - 20 °C

2.2: 1 h / 20 °C

3.1: N-Bromosuccinimide / dichloromethane / 2.25 h / -5 - 20 °C

3.2: 20 °C

4.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.17 h / 135 °C

5.1: sulfuric acid / ethanol / 20 °C / Reflux

6.1: pyridine / dichloromethane / 20 °C

6.2: 20 °C

6.3: 2 h / 60 °C

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-Bromosuccinimide; sulfuric acid; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane;

upstream raw materials:

2-bromo-4-chloro-1-fluorobenzene

3-bromo-5-chloro-2-fluorobenzoic acid

3-bromo-5-chloro-2-fluorobenzaldehyde

methyl 3-bromo-5-chloro-2-fluorobenzoate

Downstream raw materials:

N-(5-chloro-3-(2-cyclopropyl-5-(2-(methylsulfinyl)pyrimidin-4-yl)oxazol-4-yl)-2-fluorophenyl)methanesulfonamide

(S)-tert-butyl-1-(4-(4-(5-chloro-2-fluoro-3-(methylsulfonamido)phenyl)-2-cyclopropyloxazol-5-yl)pyrimidin-2-ylamino)propan-2-ylcarbamate

Refernces