N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)-2-chloro-3-(1-cyanocyclopropyl)benzamide

Base Information

Chemical Name:N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)-2-chloro-3-(1-cyanocyclopropyl)benzamide
CAS No.:1125633-37-5
Molecular Formula:C₂₅H₁₇ClFN₅O₃S
Molecular Weight:521.959
Hs Code.:

Synonyms:N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)-2-chloro-3-(1-cyanocyclopropyl)benzamide

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Chemical Property of N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)-2-chloro-3-(1-cyanocyclopropyl)benzamide

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Technology Process of N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)-2-chloro-3-(1-cyanocyclopropyl)benzamide

There total 9 articles about N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)-2-chloro-3-(1-cyanocyclopropyl)benzamide 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: 54.0%

: 1125632-92-9
2-chloro-3-(1-cyanocyclopropyl)benzoic acid chloride

: 1125632-09-8
N-[5-(3-amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]acetamide

: 1125633-37-5
N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)-2-chloro-3-(1-cyanocyclopropyl)benzamide

Guidance literature:: In tetrahydrofuran; N,N-dimethyl acetamide; at 20 ℃; Cooling with ice;
DOI:10.1016/j.bmc.2012.06.015

Reference yield:

: 62257-16-3
5-hydroxy-2-fluoroaniline

: 1125633-37-5
N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)-2-chloro-3-(1-cyanocyclopropyl)benzamide

Guidance literature:: Multi-step reaction with 7 steps

1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

2: tetrahydrofuran / 12 h / Reflux

3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 12 h / 20 °C

4: bromine; acetic acid / 20 °C / Cooling with ice

5: pyridine; dmap / 20 °C / Cooling with ice

6: trifluoroacetic acid / 0.5 h / 20 °C

7: tetrahydrofuran; N,N-dimethyl acetamide / 20 °C / Cooling with ice

With pyridine; dmap; palladium 10% on activated carbon; hydrogen; bromine; potassium carbonate; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2012.06.015

Reference yield:

: 4548-45-2
2-chloro-5-nitropyridine

: 1125633-37-5
N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)-2-chloro-3-(1-cyanocyclopropyl)benzamide

Guidance literature:: Multi-step reaction with 7 steps

1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C

2: tetrahydrofuran / 12 h / Reflux

3: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 12 h / 20 °C

4: bromine; acetic acid / 20 °C / Cooling with ice

5: pyridine; dmap / 20 °C / Cooling with ice

6: trifluoroacetic acid / 0.5 h / 20 °C

7: tetrahydrofuran; N,N-dimethyl acetamide / 20 °C / Cooling with ice

With pyridine; dmap; palladium 10% on activated carbon; hydrogen; bromine; potassium carbonate; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N-dimethyl acetamide; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2012.06.015