6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]nicotinonitrile

Base Information

• Chemical Name: 6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]nicotinonitrile
• CAS No.: 1057676-76-2
• Molecular Formula: C₂₅H₂₂N₆
• Molecular Weight: 406.49
• Mol file: 1057676-76-2.mol

Synonyms:6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]nicotinonitrile

Chemical Property of 6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]nicotinonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]nicotinonitrile

There total 3 articles about 6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]nicotinonitrile 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: 51.0%

1-benzyl-4-chlorophthalazine (40848-53-1) + 6-piperazin-1-yl-nicotinonitrile (149554-29-0) → 6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]nicotinonitrile (1057676-76-2)

Guidance literature:

With triethylamine; In 1-methyl-pyrrolidin-2-one; at 180 ℃; for 0.5h; Microwave irradiation; Inert atmosphere;

DOI:10.1021/jm900309j

Reference yield:

tert-butyl 4-(5-cyanopyridine-2-yl)piperazine-1-carboxylate (683274-61-5) → 6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]nicotinonitrile (1057676-76-2)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 3.5 h / 20 °C

2: triethylamine / 1,4-dioxane / 40 h / 160 - 180 °C

With triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jm500338n

Reference yield:

6-chloronicotinonitrile (33252-28-7) → 6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]nicotinonitrile (1057676-76-2)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; tetrakis(actonitrile)copper(I) hexafluorophosphate / dimethyl sulfoxide / 3 h / 140 °C

2: trifluoroacetic acid / dichloromethane / 3.5 h / 20 °C

3: triethylamine / 1,4-dioxane / 40 h / 160 - 180 °C

With tetrakis(actonitrile)copper(I) hexafluorophosphate; potassium carbonate; triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm500338n

upstream raw materials:

1-benzyl-4-chlorophthalazine

6-piperazin-1-yl-nicotinonitrile

tert-butyl 4-(5-cyanopyridine-2-yl)piperazine-1-carboxylate

6-chloronicotinonitrile

Downstream raw materials:

N-{6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]pyridin-3-ylmethyl}acetamide

1-{6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]pyridin-3-yl}-1-methylethylamine

{6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]pyridin-3-yl}methylamine

Refernces

• 1、 Miller-Moslin, Karen,Peukert, Stefan,Jain, Rishi K.,McEwan, Michael A.,Karki, Rajesh,Llamas, Luis,Yusuff, Naeem,He, Feng,Li, Yanhong,Sun, Yingchuan,Dai, Miao,Perez, Lawrence,Michael, Walter,Sheng, Tao,Lei, Huangshu,Zhang, Rui,Williams, Juliet,Bourret, Aaron,Ramamurthy, Arun,Yuan, Jing,Guo, Ribo,Matsumoto, Melissa,Vattay, Anthony,Maniara, Wieslawa,Amaral, Adam,Dorsch, Marion,Kelleher III, Joseph F.. "1-Amino-4-benzylphthalazines as orally bioavailable smoothened antagonists with antitumor activity". experimental part. p. 3954 - 3968. Retrieved 2010/01/16.