N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Base Information

• Chemical Name: N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine
• CAS No.: 475174-92-6
• Molecular Formula: C₂₂H₂₇N₃O
• Molecular Weight: 349.476
• Mol file: 475174-92-6.mol

Synonyms:N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Chemical Property of N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine

There total 8 articles about N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine 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:

C27H35N3O3 → N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine (475174-92-6)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 20 - 40 ℃; for 1h;

DOI:10.1021/jm300259r

Reference yield:

2-bromo-pyridine (109-04-6) → N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine (475174-92-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / diethylamine / 10 h / 20 °C

2.1: dichloromethane / 1 h / 0 °C / Cooling with ice

3.1: sodium methylate / methanol / 0.5 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

4.2: 0.17 h / -78 °C / Inert atmosphere

5.1: nitronium tetrafluoborate / acetonitrile / 0.17 h / 0 °C / Cooling with ice

6.1: acetic acid; zinc / ethanol; water / 0.33 h / 20 - 60 °C

7.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C / Cooling with ice

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane; water / 14 h / 90 °C / Inert atmosphere

9.1: sodium hydride / N,N-dimethyl-formamide

9.2: 1 h / 20 - 40 °C

10.1: hydrogenchloride / ethyl acetate / 1 h / 20 - 40 °C

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; nitronium tetrafluoborate; sodium methylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; diethylamine; N,N-dimethyl-formamide; acetonitrile; 8.1: Suzuki coupling;

DOI:10.1021/jm300259r

Reference yield:

N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate (475174-67-5) → N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine (475174-92-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium methylate / methanol / 0.5 h / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 0.17 h / -78 °C / Inert atmosphere

3.1: nitronium tetrafluoborate / acetonitrile / 0.17 h / 0 °C / Cooling with ice

4.1: acetic acid; zinc / ethanol; water / 0.33 h / 20 - 60 °C

5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C / Cooling with ice

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane; water / 14 h / 90 °C / Inert atmosphere

7.1: sodium hydride / N,N-dimethyl-formamide

7.2: 1 h / 20 - 40 °C

8.1: hydrogenchloride / ethyl acetate / 1 h / 20 - 40 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; nitronium tetrafluoborate; sodium methylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 6.1: Suzuki coupling;

DOI:10.1021/jm300259r

upstream raw materials:

2-bromo-pyridine

2-ethylpyrazolo[1,5-a]pyridine

N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate

7-bromo-2-ethylpyrazolo[1,5-a]pyridine-3-amine

Downstream raw materials:

N-(cyclopropylmethyl)-2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)-N-[(tetrahydro-2H-pyran-4-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine