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

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Chemical Name:N-(cyclopropylmethyl)-2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)-N-[(tetrahydrofuran-3-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine
CAS No.:475171-70-1
Molecular Formula:C₂₇H₃₅N₃O₂
Molecular Weight:433.594
Hs Code.:

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

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

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

There total 9 articles about N-(cyclopropylmethyl)-2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)-N-[(tetrahydrofuran-3-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: 92.0%

: 7-bromo-N-(cyclopropylmethyl)-2-ethyl-N-((tetrahydrofuran-3-yl)methyl)pyrazolo[1,5-a]pyridin-3-amine

: 355836-08-7
2-methoxy-4,6-dimethylbenzeneboronic acid

: 475171-70-1
N-(cyclopropylmethyl)-2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)-N-[(tetrahydrofuran-3-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; water; at 90 ℃; for 14h; Inert atmosphere;
DOI:10.1021/jm300259r

Reference yield:

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

: 475171-70-1
N-(cyclopropylmethyl)-2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)-N-[(tetrahydrofuran-3-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: 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 / 20 °C

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

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; 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

: 475171-70-1
N-(cyclopropylmethyl)-2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)-N-[(tetrahydrofuran-3-yl)methyl]pyrazolo[1,5-a]pyridin-3-amine

Guidance literature:: Multi-step reaction with 2 steps

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

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

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