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

Base Information

Chemical Name:N-(cyclopropylmethyl)-7-(2,6-dimethoxy-4-methylphenyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine
CAS No.:475171-98-3
Molecular Formula:C₂₈H₃₇N₃O₃
Molecular Weight:463.62
Hs Code.:

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

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Chemical Property of N-(cyclopropylmethyl)-7-(2,6-dimethoxy-4-methylphenyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine

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Technology Process of N-(cyclopropylmethyl)-7-(2,6-dimethoxy-4-methylphenyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine

There total 9 articles about N-(cyclopropylmethyl)-7-(2,6-dimethoxy-4-methylphenyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]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:

: 50675-18-8
3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde

: C₂₂H₂₇N₃O₂

: 475171-98-3
N-(cyclopropylmethyl)-7-(2,6-dimethoxy-4-methylphenyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine

Guidance literature:: With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jm300259r

Reference yield:

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

: 475171-98-3
N-(cyclopropylmethyl)-7-(2,6-dimethoxy-4-methylphenyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]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: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane; water / 14 h / 90 °C / Inert atmosphere

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

6.2: 1 h / 20 - 40 °C

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

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

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; nitronium tetrafluoborate; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; acetic acid; triethylamine; zinc; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 5.1: Suzuki coupling;
DOI:10.1021/jm300259r

Reference yield:

: 176528-19-1
[2,6-dimethoxy-4-methylphenyl]boronic acid

: 475171-98-3
N-(cyclopropylmethyl)-7-(2,6-dimethoxy-4-methylphenyl)-2-ethyl-N-[(tetrahydro-2H-pyran-4-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine

Guidance literature:: Multi-step reaction with 4 steps

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

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

2.2: 1 h / 20 - 40 °C

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

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

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water; ethyl acetate; N,N-dimethyl-formamide; 1.1: Suzuki coupling;
DOI:10.1021/jm300259r