N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide trifluoroacetate

Base Information

• Chemical Name: N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide trifluoroacetate
• CAS No.: 1307271-95-9
• Molecular Formula: C₂HF₃O₂*C₂₃H₂₇ClFN₅O₂S₂
• Molecular Weight: 638.107

Synonyms:N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide trifluoroacetate

Chemical Property of N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide trifluoroacetate

Chemical Property:

Purity/Quality:

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Technology Process of N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide trifluoroacetate

There total 12 articles about N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide trifluoroacetate 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:

3-bromo-2-fluorobenzoic acid (161957-56-8) → N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide trifluoroacetate (1307271-95-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sulfuric acid / 1 h / Inert atmosphere; Reflux

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

2.2: 1 h / 20 °C / Inert atmosphere

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

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

4.2: 1.33 h / 0 - 20 °C / Inert atmosphere

5.1: N-Bromosuccinimide / ISOPROPYLAMIDE / 0.83 h / 20 °C / Inert atmosphere

5.2: 0.5 h / 80 °C / Inert atmosphere

6.1: tri-n-butyl-tin hydride; water / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 1 h / 20 °C / Inert atmosphere

7.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

8.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

9.1: sodium cyanoborohydride / water; methanol / 1 h / 20 °C / Inert atmosphere

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

Reference yield:

2-fluoro-3-nitrobenzoic acid methyl ester (946126-94-9) → N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide trifluoroacetate (1307271-95-9)

Guidance literature:

Multi-step reaction with 8 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 / 0.83 h / 20 °C / Inert atmosphere

4.2: 0.5 h / 80 °C / Inert atmosphere

5.1: tri-n-butyl-tin hydride; water / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 1 h / 20 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

8.1: sodium cyanoborohydride / water; methanol / 1 h / 20 °C / Inert atmosphere

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

Reference yield:

2-fluoro-3-bromobenzoic acid methyl ester (206551-41-9) → N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide trifluoroacetate (1307271-95-9)

Guidance literature:

Multi-step reaction with 8 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 / 0.83 h / 20 °C / Inert atmosphere

4.2: 0.5 h / 80 °C / Inert atmosphere

5.1: tri-n-butyl-tin hydride; water / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 1 h / 20 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

8.1: sodium cyanoborohydride / water; methanol / 1 h / 20 °C / Inert atmosphere

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

upstream raw materials:

3-bromo-2-fluorobenzoic acid

2-fluoro-3-nitrobenzoic acid methyl ester

2-fluoro-3-bromobenzoic acid methyl ester

2-fluoro-3-nitrotoluene

Downstream raw materials:

N-{3-[5-(2-amino-4-pyrimidinyl)-2-(1,4-dimethyl-4-piperidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-propanesulfonamide hydrochloride

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