1-(4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(4-((6-(methylamino)pyrimidin-4-yl)oxy)phenyl)urea

Base Information

• Chemical Name: 1-(4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(4-((6-(methylamino)pyrimidin-4-yl)oxy)phenyl)urea
• CAS No.: 630124-46-8
• Molecular Formula: C26H30F3N7O2
• Molecular Weight: 529.56
• UNII: W34UO2M4T6
• ChEMBL ID: CHEMBL574738
• DSSTox Substance ID: DTXSID70212239
• Pharos Ligand ID: HJKNQGK5SMHN
• Wikidata: Q27074554
• Mol file: 630124-46-8.mol

Synonyms:1-(4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(4-((6-(methylamino)pyrimidin-4-yl)oxy)phenyl)urea;AST 487;NVP-AST487

Chemical Property of 1-(4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(4-((6-(methylamino)pyrimidin-4-yl)oxy)phenyl)urea

Chemical Property:

• Boiling Point: 563.1±50.0 °C(Predicted)
• PKA: 13.33±0.70(Predicted)
• PSA: 94.65000
• Density: 1.341±0.06 g/cm3(Predicted)
• LogP: 5.20570
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 529.24130771
• Heavy Atom Count: 38
• Complexity: 730

Purity/Quality:

99% ^*data from raw suppliers

NVP-AST487 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCN(CC1)CC2=C(C=C(C=C2)NC(=O)NC3=CC=C(C=C3)OC4=NC=NC(=C4)NC)C(F)(F)F
• Uses: AST-487 is an inhibitor of RET (IC50 = 0.88 μM), FLT3 (Ki = 0.52 μM), KDR (IC50 = 0.17 μM), c-Abl (IC50 = 0.02 μM), and c-Kit (IC50 = 0.5 μM). It has been shown to inhibit RET autophosphorylation and activation of downstream effectors and to prevent the growth of human thyroid cancer cell lines with activating mutations of RET but not of lines without RET mutations. In xenografts of NIH3T3 cells expressing oncogenic RET and of the MTC cell line TT in nude mice, AST-487 dose dependently inhibited tumor growth. It also demonstrates antiproliferative effects on primary cells from acute myelocytic leukemia patients and on cell lines expressing FLT3-ITD or FLT3 kinase domain point mutants.[Cayman Chemical] N-[4-[(4-Ethyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]-N''-[4-[[6-(methylamino)-4-pyrimidinyl]oxy]phenyl]urea is an inhibitor of RET, FLT3, KDR, c-Abl and c-Kit. Also, it prevent the growth of human thyroid cancer cells. It is a COVID19-related research product.

Technology Process of 1-(4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(4-((6-(methylamino)pyrimidin-4-yl)oxy)phenyl)urea

There total 18 articles about 1-(4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-(4-((6-(methylamino)pyrimidin-4-yl)oxy)phenyl)urea 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: 96.0%

4-(4-ethylpiperazin-1-ylmethyl)-3-trifluoromethylphenylamine (630125-91-6) + C18H16N4O3 → AST-487 (630124-46-8)

Guidance literature:

In dimethyl sulfoxide; at 100 ℃;

DOI:10.1021/op800136f

Reference yield: 94.0%

4-(4-ethylpiperazin-1-ylmethyl)-3-trifluoromethylphenylamine (630125-91-6) + C18H16N4O3 → AST-487 (630124-46-8) + C23H22N8O3

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; Temperature; Solvent; Reagent/catalyst;

DOI:10.1021/op800136f

Reference yield: 86.0%

[4-(4-ethylpiperazin-1-ylmethyl)-3-trifluoromethylphenyl]carbamic acid phenyl ester hydrochloride + [6-(4-aminophenoxy)pyrimidin-4-yl]methylamine → AST-487 (630124-46-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60 ℃; for 2h;

DOI:10.1021/op800136f

upstream raw materials:

4-amino-2-trifluoromethylbenzonitrile

4-amino-2-(trifluoromethyl)benzaldehyde

4-nitrophenol sodium salt

4-(4-ethylpiperazin-1-ylmethyl)-3-trifluoromethylphenylamine