1,1-dimethylethyl 4-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate

Base Information

• Chemical Name: 1,1-dimethylethyl 4-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate
• CAS No.: 1195769-63-1
• Molecular Formula: C₂₄H₂₇ClFN₅O₂S
• Molecular Weight: 504.028

Synonyms:1,1-dimethylethyl 4-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate

Chemical Property of 1,1-dimethylethyl 4-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,1-dimethylethyl 4-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate

There total 11 articles about 1,1-dimethylethyl 4-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate 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: 56.0%

1,1-dimethylethyl 4-[5-(2-chloro-4-pyrimidinyl)-4-(2-fluoro-3-{[(2-propen-1-yloxy)carbonyl]amino}phenyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate (1195769-62-0) → 1,1-dimethylethyl 4-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate (1195769-63-1)

Guidance literature:

With water; tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

Reference yield:

3-bromo-2-fluorobenzoic acid (161957-56-8) → 1,1-dimethylethyl 4-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate (1195769-63-1)

Guidance literature:

Multi-step reaction with 6 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

With N-Bromosuccinimide; tert-butyl carbazate; sulfuric acid; water; tri-n-butyl-tin hydride; sodium hydrogencarbonate; caesium carbonate; 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;

Reference yield:

2-fluoro-3-nitrobenzoic acid methyl ester (946126-94-9) → 1,1-dimethylethyl 4-[4-(3-amino-2-fluorophenyl)-5-(2-chloro-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate (1195769-63-1)

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 / 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

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

upstream raw materials:

1,1-dimethylethyl 4-[5-(2-chloro-4-pyrimidinyl)-4-(2-fluoro-3-{[(2-propen-1-yloxy)carbonyl]amino}phenyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate

3-bromo-2-fluorobenzoic acid

2-fluoro-3-nitrobenzoic acid methyl ester

2-fluoro-3-bromobenzoic acid methyl ester

Downstream raw materials:

1,1-dimethylethyl 4-[5-(2-chloro-4-pyrimidinyl)-4-(3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate

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

1,1-dimethylethyl 4-(5-(2-chloro-4-pyrimidinyl)-4-{2-fluoro-3-[(propylsulfonyl)amino]phenyl}-1,3-thiazol-2-yl)-4-methyl-1-piperidinecarboxylate

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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