3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-1-(piperazin-1-yl)propan-1-one hydrochloride

Base Information

• Chemical Name: 3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-1-(piperazin-1-yl)propan-1-one hydrochloride
• CAS No.: 1401728-40-2
• Molecular Formula: C₂₄H₃₁N₅O*ClH
• Molecular Weight: 442.004
• Mol file: 1401728-40-2.mol

Synonyms:3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-1-(piperazin-1-yl)propan-1-one hydrochloride

Chemical Property of 3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-1-(piperazin-1-yl)propan-1-one hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-1-(piperazin-1-yl)propan-1-one hydrochloride

There total 7 articles about 3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-1-(piperazin-1-yl)propan-1-one hydrochloride 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: 98.0%

tert-butyl 4-(3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)propanoyl)piperazine-1-carboxylate (1401729-02-9) → 3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-1-(piperazin-1-yl)propan-1-one hydrochloride (1401728-40-2)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b01703

Reference yield:

(E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]acrylic acid methyl ester (1401728-64-0) → 3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-1-(piperazin-1-yl)propan-1-one hydrochloride (1401728-40-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hydroxide / tetrahydrofuran; water / 60 h / 20 °C / Inert atmosphere

1.2: pH Ca_. 3.5 / Inert atmosphere

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 1 h / 20 °C

4.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C / Inert atmosphere

With hydrogenchloride; 20% palladium hydroxide-activated charcoal; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1021/acs.jmedchem.6b01703

Reference yield:

3-(4-Bromo-phenyl)-propionitrile (57775-08-3) → 3-(4-((2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenyl)-1-(piperazin-1-yl)propan-1-one hydrochloride (1401728-40-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium 2-methylbutan-2-olate / tetrahydrofuran; toluene / 0.33 h / 20 °C / Inert atmosphere

2.1: hydrazine hydrate; acetic acid / ethanol / 0.25 h / 140 °C / Inert atmosphere; Microwave irradiation

2.2: 0.5 h / 160 °C / Inert atmosphere; Microwave irradiation

3.1: trifluoroacetic acid / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere

4.1: N-Methyldicyclohexylamine; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane / 0.25 h / 130 °C / Inert atmosphere; Microwave irradiation

5.1: lithium hydroxide / tetrahydrofuran; water / 60 h / 20 °C / Inert atmosphere

5.2: pH Ca_. 3.5 / Inert atmosphere

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

7.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 1 h / 20 °C

8.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C / Inert atmosphere

With hydrogenchloride; bis(tri-t-butylphosphine)palladium⁽⁰⁾; hydrazine hydrate; N-Methyldicyclohexylamine; 20% palladium hydroxide-activated charcoal; hydrogen; potassium 2-methylbutan-2-olate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; toluene; 4.1: |Heck Reaction;

DOI:10.1021/acs.jmedchem.6b01703

upstream raw materials:

3-(4-Bromo-phenyl)-propionitrile

2-(4-bromobenzyl)-3-oxopentanenitrile

4-(4-bromobenzyl)-5-ethyl-2H-pyrazol-3-ylamine

(E)-3-[4-(2-ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-ylmethyl)phenyl]acrylic acid methyl ester