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

Base Information

• Chemical Name: N-[6-(4-amino-2-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide
• CAS No.: 1195782-31-0
• Molecular Formula: C₁₇H₁₅ClN₄O₂
• Molecular Weight: 342.785
• Mol file: 1195782-31-0.mol

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

Chemical Property of N-[6-(4-amino-2-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[6-(4-amino-2-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

There total 10 articles about N-[6-(4-amino-2-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide 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:

C17H13ClN4O4 → N-[6-(4-amino-2-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (1195782-31-0)

Guidance literature:

With iron; ammonium chloride; In tetrahydrofuran; ethanol; water; at 80 ℃; for 7h;

Reference yield:

6-chloropyridine-3-ol (41288-96-4) → N-[6-(4-amino-2-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (1195782-31-0)

Guidance literature:

Multi-step reaction with 9 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 / 6 h / 20 °C

9.1: iron; ammonium chloride / tetrahydrofuran; ethanol; water / 7 h / 80 °C

With pyridine; iron; potassium carbonate; ammonium chloride; caesium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetic anhydride; lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; CyJohnPhos; In tetrahydrofuran; ethanol; ISOPROPYLAMIDE; α,α,α-trifluorotoluene; water; dimethyl sulfoxide; methoxybenzene; N,N-dimethyl-formamide;

Reference yield:

2-chloro-5-[(4-methoxybenzyl)oxy]pyridine (1195782-12-7) → N-[6-(4-amino-2-chlorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (1195782-31-0)

Guidance literature:

Multi-step reaction with 8 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 / 6 h / 20 °C

8.1: iron; ammonium chloride / tetrahydrofuran; ethanol; water / 7 h / 80 °C

With pyridine; iron; ammonium chloride; caesium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetic anhydride; lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; CyJohnPhos; In tetrahydrofuran; ethanol; ISOPROPYLAMIDE; α,α,α-trifluorotoluene; water; dimethyl sulfoxide; methoxybenzene; N,N-dimethyl-formamide;

upstream raw materials:

6-chloropyridine-3-ol

3-chloro-4-fluoronitrobenzene

2-chloro-5-[(4-methoxybenzyl)oxy]pyridine

5-[(4-methoxybenzyl)oxy]pyridine-2-amine

Downstream raw materials:

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