N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Base Information

• Chemical Name: N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
• CAS No.: 1195779-48-6
• Molecular Formula: C₃₁H₂₆FN₅O₄
• Molecular Weight: 551.577
• Mol file: 1195779-48-6.mol

Synonyms:N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Chemical Property of N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

There total 17 articles about N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide 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: 49.0%

N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (1195781-23-7) + 1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (91540-63-5) → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (1195779-48-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

6-chloropyridine-3-ol (41288-96-4) → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (1195779-48-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C

2.1: lithium hexamethyldisilazane / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; CyJohnPhos / tetrahydrofuran / 20 - 80 °C / Inert atmosphere

2.2: 1 h / 20 °C

3.1: pyridine / 0 - 20 °C

4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 60 °C

5.1: trifluoroacetic anhydride / tetrahydrofuran / 1 h / 0 °C

5.2: 3 h / 20 °C / pH 12 - 13

6.1: ISOPROPYLAMIDE / 3 h / 0 °C

7.1: trifluoroacetic acid / α,α,α-trifluorotoluene; methoxybenzene / 3 h / 20 °C

8.1: caesium carbonate / dimethyl sulfoxide / 5 h / 20 °C / Inert atmosphere

9.1: hydrazine hydrate / tetrahydrofuran; methanol / 16 h / activated carbon; Reflux

10.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C

With pyridine; potassium carbonate; caesium carbonate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; trifluoroacetic anhydride; lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; CyJohnPhos; In tetrahydrofuran; methanol; ISOPROPYLAMIDE; α,α,α-trifluorotoluene; dimethyl sulfoxide; methoxybenzene; N,N-dimethyl-formamide;

Reference yield:

2-chloro-5-[(4-methoxybenzyl)oxy]pyridine (1195782-12-7) → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (1195779-48-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium hexamethyldisilazane / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; CyJohnPhos / tetrahydrofuran / 20 - 80 °C / Inert atmosphere

1.2: 1 h / 20 °C

2.1: pyridine / 0 - 20 °C

3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 60 °C

4.1: trifluoroacetic anhydride / tetrahydrofuran / 1 h / 0 °C

4.2: 3 h / 20 °C / pH 12 - 13

5.1: ISOPROPYLAMIDE / 3 h / 0 °C

6.1: trifluoroacetic acid / α,α,α-trifluorotoluene; methoxybenzene / 3 h / 20 °C

7.1: caesium carbonate / dimethyl sulfoxide / 5 h / 20 °C / Inert atmosphere

8.1: hydrazine hydrate / tetrahydrofuran; methanol / 16 h / activated carbon; Reflux

9.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C

With pyridine; caesium carbonate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; trifluoroacetic anhydride; lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; CyJohnPhos; In tetrahydrofuran; methanol; ISOPROPYLAMIDE; α,α,α-trifluorotoluene; dimethyl sulfoxide; methoxybenzene; N,N-dimethyl-formamide;

upstream raw materials:

N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

1-(2,6-dimethylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

6-chloropyridine-3-ol

3,4-difluoronitrobenzene

Refernces