N-{5-[(5-aminopyridine-2-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide

Base Information

• Chemical Name: N-{5-[(5-aminopyridine-2-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide
• CAS No.: 1125632-16-7
• Molecular Formula: C₂₂H₁₆ClFN₄O₂
• Molecular Weight: 422.846
• Mol file: 1125632-16-7.mol

Synonyms:N-{5-[(5-aminopyridine-2-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide

Chemical Property of N-{5-[(5-aminopyridine-2-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{5-[(5-aminopyridine-2-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide

There total 8 articles about N-{5-[(5-aminopyridine-2-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: 69.0%

2-chloro-3-(1-cyanocycropropyl)-N-{2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (1125632-15-6) → N-{5-[(5-aminopyridine-2-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide (1125632-16-7)

Guidance literature:

With iron; calcium chloride; In ethanol; water; at 80 ℃; for 18h;

DOI:10.1021/jm300126x

Reference yield:

2-chloro-3-(1-cyanocyclopropyl)-N-(2-fluoro-5-hydroxyphenyl)benzamide (1125632-14-5) → N-{5-[(5-aminopyridine-2-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide (1125632-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C

2: iron; calcium chloride / ethanol; water / 18 h / 80 °C

With iron; potassium carbonate; calcium chloride; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm300126x

Reference yield:

methyl 2-chloro-3-methylbenzoate (920759-93-9) → N-{5-[(5-aminopyridine-2-yl)oxy]-2-fluorophenyl}-2-chloro-3-(1-cyanocyclopropyl)benzamide (1125632-16-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile / 26 h / 90 °C

2.1: N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere

3.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.33 h / 20 °C / Cooling with ice

3.2: 16 h / 20 °C

4.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 18 h / 20 °C

5.1: thionyl chloride

6.1: sodium hydrogencarbonate / tetrahydrofuran; water / 20 °C

7.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C

8.1: iron; calcium chloride / ethanol; water / 18 h / 80 °C

With N-Bromosuccinimide; thionyl chloride; lithium hydroxide monohydrate; 2,2'-azobis(isobutyronitrile); water; iron; sodium hydride; sodium hydrogencarbonate; potassium carbonate; calcium chloride; In tetrahydrofuran; methanol; ethanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1021/jm300126x

upstream raw materials:

methyl 2-chloro-3-methylbenzoate

methyl 3-(bromomethyl)-2-chlorobenzoate

2-chloro-3-(1-cyanocyclopropyl)-N-(2-fluoro-5-hydroxyphenyl)benzamide

2-chloro-3-(1-cyanocycropropyl)-N-{2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

Downstream raw materials:

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