N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2’-fluoro-3-methyl-2,4’-bipyridin-5-yl)acetamide

Base Information

• Chemical Name: N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2’-fluoro-3-methyl-2,4’-bipyridin-5-yl)acetamide
• CAS No.: 1243245-18-2
• Molecular Formula: C₂₄H₂₅FN₆O₂
• Molecular Weight: 448.5

Synonyms:N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2’-fluoro-3-methyl-2,4’-bipyridin-5-yl)acetamide

Chemical Property of N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2’-fluoro-3-methyl-2,4’-bipyridin-5-yl)acetamide

Chemical Property:

• Melting Point: >174°C (dec.)

Purity/Quality:

97% ^*data from raw suppliers

GNF-6231 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: GNF-6231 was used in the study to prepare N-?(hetero)?aryl, 2-?(hetero)?aryl-?substituted acetamides for use as Wnt signaling modulators. Blockade of aberrant Wnt signaling is an attractive therapeutic approach in multiple cancers.

Technology Process of N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2’-fluoro-3-methyl-2,4’-bipyridin-5-yl)acetamide

There total 3 articles about N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2’-fluoro-3-methyl-2,4’-bipyridin-5-yl)acetamide 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: 61.0%

1-(4-(6-aminopyridin-3-yl)piperazin-1-yl)ethan-1-one (959795-77-8) + 2-(2'-fluoro-3-methyl-2,4'-bipyridin-5-yl)acetic acid (1243246-17-4) → N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2’-fluoro-3-methyl-2,4’-bipyridin-5-yl)acetamide (1243245-18-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/acsmedchemlett.6b00038

Reference yield:

5-bromo-2-chloro-3-methylpyridine (29241-60-9) → N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2’-fluoro-3-methyl-2,4’-bipyridin-5-yl)acetamide (1243245-18-2)

Guidance literature:

Multi-step reaction with 4 steps

1: bis(dibenzylideneacetone)-palladium⁽⁰⁾; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene / tetrahydrofuran; diethyl ether / 4 h / 70 °C / Inert atmosphere; Sealed tube

2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / iso-butanol / 2 h / 100 °C

4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; palladium diacetate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; iso-butanol;

DOI:10.1021/acsmedchemlett.6b00038

Reference yield:

tert-butyl 2-(6-chloro-5-methylpyridin-3-yl)acetate (1243245-77-3) → N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2’-fluoro-3-methyl-2,4’-bipyridin-5-yl)acetamide (1243245-18-2)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

2: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / iso-butanol / 2 h / 100 °C

3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 20 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; iso-butanol;

DOI:10.1021/acsmedchemlett.6b00038

upstream raw materials:

1-(4-(6-aminopyridin-3-yl)piperazin-1-yl)ethan-1-one

2-(2'-fluoro-3-methyl-2,4'-bipyridin-5-yl)acetic acid

tert-butyl 2-(6-chloro-5-methylpyridin-3-yl)acetate

5-bromo-2-chloro-3-methylpyridine

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