5-Amino-1-tert-butyl-3-(1'-naphthylmethyl)-4-cyanopyrazole

Base Information

• Chemical Name: 5-Amino-1-tert-butyl-3-(1'-naphthylmethyl)-4-cyanopyrazole
• CAS No.: 221243-77-2
• Molecular Formula: C19H20N4
• Molecular Weight: 304.39
• ChEMBL ID: CHEMBL1865574
• DSSTox Substance ID: DTXSID50407808
• Wikidata: Q27164262
• Mol file: 221243-77-2.mol

Synonyms:221243-77-2;5-Amino-1-tert-butyl-3-(1'-naphthylmethyl)-4-cyanopyrazole;5-amino-1-tert-butyl-3-(naphthalen-1-ylmethyl)pyrazole-4-carbonitrile;5-aMino-1-(tert-butyl)-3-(naphthalen-1-ylMethyl)-1H-pyrazole-4-carbonitrile;4-AMINO-1-TERT-BUTYL-3-(1'-NAPHTHYLMETHYL)-4-CYANOPYRAZOLE;HMS2196D09;MLS001065849;CHEMBL1865574;CHEBI:92532;DTXSID50407808;HMS3340F08;AKOS030240382;SMR000486338;FT-0661643;J-014531;Q27164262;5-amino-1-tert-butyl-3-(1-naphthalenylmethyl)-4-pyrazolecarbonitrile;5-amino-1-tert-butyl-3-(naphthalen-1-ylmethyl)-1H-pyrazole-4-carbonitrile;5-Amino-1-tert-butyl-3-(1 inverted exclamation mark -naphthylmethyl)-4-cyanopyrazole;5-amino-1-tert-butyl-3-[(naphthalen-1-yl)methyl]-1H-pyrazole-4-carbonitrile

Chemical Property of 5-Amino-1-tert-butyl-3-(1'-naphthylmethyl)-4-cyanopyrazole

Chemical Property:

• Vapor Pressure: 8.99E-11mmHg at 25°C
• Refractive Index: 1.622
• Boiling Point: 516.4 °C at 760 mmHg
• Flash Point: 266.1 °C
• PSA: 67.63000
• Density: 1.14 g/cm³
• LogP: 4.41718
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 304.16879665
• Heavy Atom Count: 23
• Complexity: 460

Purity/Quality:

99% ^*data from raw suppliers

5-Amino-1-tert-butyl-3-(1’-naphthylmethyl)-4-cyanopyrazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)N1C(=C(C(=N1)CC2=CC=CC3=CC=CC=C32)C#N)N
• Uses: A highly potent (IC50=1.5nM) and uniquely specific tyrosine kinase inhibitor of a rationally engineered v-Src tyrosine kinase

Technology Process of 5-Amino-1-tert-butyl-3-(1'-naphthylmethyl)-4-cyanopyrazole

There total 7 articles about 5-Amino-1-tert-butyl-3-(1'-naphthylmethyl)-4-cyanopyrazole 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:

naphthalen-1-yl-acetyl chloride (5121-00-6) → 5-amino-1-tert-butyl-3-naphthalen-1-ylmethyl-1H-pyrazole-4-carbonitrile (221243-77-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / tetrahydrofuran / 0.5 h / Ambient temperature

2: aq. NaHCO₃ / dioxane / 1 h / 80 °C

3: Et₃N / ethanol / 1 h / Heating

With sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol;

DOI:10.1021/ja983267v

Reference yield:

tertbutylhydrazine hydrochloride (7400-27-3) + 2-(1-methoxy-2-naphthalen-1-ylethylidene)malononitrile (221243-13-6) → 5-amino-1-tert-butyl-3-naphthalen-1-ylmethyl-1H-pyrazole-4-carbonitrile (221243-77-2)

Guidance literature:

With triethylamine; In ethanol; for 1h; Heating;

DOI:10.1021/ja983267v

Reference yield:

naphth-1-yl acetic acid (86-87-3) → 5-amino-1-tert-butyl-3-naphthalen-1-ylmethyl-1H-pyrazole-4-carbonitrile (221243-77-2)

Guidance literature:

Multi-step reaction with 4 steps

1: (COCl)2, DMF / diethyl ether

2: NaH / tetrahydrofuran / 0.5 h / Ambient temperature

3: aq. NaHCO₃ / dioxane / 1 h / 80 °C

4: Et₃N / ethanol / 1 h / Heating

With oxalyl dichloride; sodium hydride; sodium hydrogencarbonate; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol;

DOI:10.1021/ja983267v

upstream raw materials:

tertbutylhydrazine hydrochloride

2-(1-methoxy-2-naphthalen-1-ylethylidene)malononitrile

naphthalen-1-yl-acetyl chloride

naphth-1-yl acetic acid

Downstream raw materials:

1-tert-butyl-3-(naphthalen-1-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Refernces

• 1、 Lourido, Sebastian,Zhang, Chao,Lopez, Michael S.,Tang, Keliang,Barks, Jennifer,Wang, Qiuling,Wildman, Scott A.,Shokat, Kevan M.,Sibley, L. David. "Optimizing small molecule inhibitors of calcium-dependent protein kinase 1 to prevent infection by toxoplasma gondii". . p. 3068 - 3077. Retrieved 2013/06/05.