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

Base Information

Chemical Name:N-(cyclopropylmethyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]-7-(2,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-amine
CAS No.:1380434-16-1
Molecular Formula:C₂₈H₃₇N₃O₄
Molecular Weight:479.619
Hs Code.:

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

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Chemical Property of N-(cyclopropylmethyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]-7-(2,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-amine

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Technology Process of N-(cyclopropylmethyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]-7-(2,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-amine

There total 8 articles about N-(cyclopropylmethyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]-7-(2,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-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: 85.0%

: 685886-48-0
7-bromo-N-(cyclopropylmethyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine

: 213698-56-7
(2,4,5-trimethoxyphenyl)boronic acid

: 1380434-16-1
N-(cyclopropylmethyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]-7-(2,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-amine

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; barium hydroxide octahydrate; In 1,2-dimethoxyethane; water; at 90 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jm300259r

Reference yield:

: 475174-65-3
2-ethylpyrazolo[1,5-a]pyridine

: 1380434-16-1
N-(cyclopropylmethyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]-7-(2,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-amine

Guidance literature:: Multi-step reaction with 8 steps

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

1.2: 0.17 h / -78 °C / Inert atmosphere

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

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

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

5.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

5.2: 1 h / 20 - 40 °C

6.1: hydrogenchloride / ethyl acetate / 0.5 h / 20 - 40 °C

7.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.5 h / 20 °C

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; barium hydroxide octahydrate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; nitronium tetrafluoborate; barium hydroxide octahydrate; sodium tris(acetoxy)borohydride; sodium hydride; acetic acid; triethylamine; zinc; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 8.1: Suzuki coupling;
DOI:10.1021/jm300259r

Reference yield:

: 685886-47-9
7-bromo-N-(cyclopropylmethyl)-2-ethylpyrazolo[1,5-a]pyridin-3-amine

: 1380434-16-1
N-(cyclopropylmethyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]-7-(2,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-amine

Guidance literature:: Multi-step reaction with 2 steps

1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 0.5 h / 20 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; barium hydroxide octahydrate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; barium hydroxide octahydrate; sodium tris(acetoxy)borohydride; In tetrahydrofuran; 1,2-dimethoxyethane; water; 2: Suzuki coupling;
DOI:10.1021/jm300259r