3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyridine-2-carbonitrile

Base Information

• Chemical Name: 3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyridine-2-carbonitrile
• CAS No.: 1380434-27-4
• Molecular Formula: C₂₈H₃₄N₄O₄
• Molecular Weight: 490.602
• Mol file: 1380434-27-4.mol

Synonyms:

Chemical Property of 3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyridine-2-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyridine-2-carbonitrile

There total 7 articles about 3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyridine-2-carbonitrile 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:

[2,6-dimethoxy-4-(methoxymethyl)phenyl]boronic acid (685886-67-3) + 3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-iodopyrazolo[1,5-a]pyridine-2-carbonitrile (1380434-56-9) → 3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyridine-2-carbonitrile (1380434-27-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; toluene; at 90 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm300259r

Reference yield:

3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]pyrazolo[1,5-a]pyridine-2-carbonitrile (1380434-55-8) → 3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyridine-2-carbonitrile (1380434-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -90 °C / Inert atmosphere

1.2: 2 h / -78 - -40 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; toluene / 3 h / 90 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium carbonate; In tetrahydrofuran; ethanol; hexane; toluene; 2.1: Suzuki coupling;

DOI:10.1021/jm300259r

Reference yield:

2-(methylsulfonyl)-3-nitropyrazolo[1,5-a]pyridine (935859-71-5) → 3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyridine-2-carbonitrile (1380434-27-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrahydrofuran; N,N-dimethyl-formamide / 6 h / 20 - 80 °C

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C / 760.05 Torr

3.1: titanium(IV) isopropylate / tetrahydrofuran / 7 h / 20 °C

3.2: 3 h / 0 - 20 °C

4.1: 2-picoline borane complex / methanol; acetic acid / 16 h / 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -90 °C / Inert atmosphere

5.2: 2 h / -78 - -40 °C

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; toluene / 3 h / 90 °C / Inert atmosphere

With titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2-picoline borane complex; palladium 10% on activated carbon; hydrogen; sodium carbonate; In tetrahydrofuran; methanol; ethanol; hexane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; 6.1: Suzuki coupling;

DOI:10.1021/jm300259r

upstream raw materials:

[2,6-dimethoxy-4-(methoxymethyl)phenyl]boronic acid

3-[(cyclopropylmethyl)[(tetrahydro-2H-pyran-4-yl)methyl]-amino]-7-iodopyrazolo[1,5-a]pyridine-2-carbonitrile

C₈H₆N₄

2-(methylsulfonyl)-3-nitropyrazolo[1,5-a]pyridine