N-(6-(4-(2-((4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-2-oxoethyl)phenoxy)pyrimidin-4-yl)cyclopropanecarboxamide

Base Information

• Chemical Name: N-(6-(4-(2-((4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-2-oxoethyl)phenoxy)pyrimidin-4-yl)cyclopropanecarboxamide
• CAS No.: 1421227-53-3
• Molecular Formula: C29H31F3N6O3
• Molecular Weight: 568.59
• DSSTox Substance ID: DTXSID901101882
• Nikkaji Number: J3.164.641C
• ChEMBL ID: CHEMBL3633033
• Mol file: 1421227-53-3.mol

Synonyms:1421227-53-3;WS6;N-(6-(4-(2-((4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-2-oxoethyl)phenoxy)pyrimidin-4-yl)cyclopropanecarboxamide;N-(6-{4-[({4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}carbamoyl)methyl]phenoxy}pyrimidin-4-yl)cyclopropanecarboxamide;4-[[6-[(Cyclopropylcarbonyl)amino]-4-pyrimidinyl]oxy]-N-[4-[(4-methyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]-benzeneacetamide;N-[6-[4-[2-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)anilino]-2-oxoethyl]phenoxy]pyrimidin-4-yl]cyclopropanecarboxamide;Benzeneacetamide, 4-[[6-[(cyclopropylcarbonyl)amino]-4-pyrimidinyl]oxy]-N-[4-[(4-methyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]-;CHEMBL3633033;SCHEMBL21939207;WS-6;WS 6;FTODTDQFHDJWIQ-UHFFFAOYSA-N;DTXSID901101882;BCP10967;EX-A2182;WGC22753;MFCD26793882;AKOS026750355;CCG-270085;CS-3447;NCGC00384169-08;AC-33128;AS-16478;HY-12461;FT-0745267;S7442;A899220;4-[[6-[(Cyclopropylcarbonyl) amino]-4-pyrimidinyl]oxy]-N-[4-[(4- methyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]-benzeneacetamide;4-[[6-[(Cyclopropylcarbonyl)amino]-4-pyrimidinyl]oxy]-N-[4-[(4-methyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]-benzeneacetam ide;4-[[6-[(Cyclopropylcarbonyl)amino]-4-pyrimidinyl]oxy]-N-[4-[(4-methyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]benzeneacetamide;N-[6-[4-[2-[[4-[(4-Methylpiperazine-1-yl)methyl]-3-(trifluoromethyl)phenyl]amino]-2-oxoethyl]phenoxy]pyrimidine-4-yl]cyclopropane-1-carboxamide

Chemical Property of N-(6-(4-(2-((4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-2-oxoethyl)phenoxy)pyrimidin-4-yl)cyclopropanecarboxamide

Chemical Property:

• Boiling Point: 744.1±60.0 °C(Predicted)
• PKA: 11.82±0.20(Predicted)
• PSA: 99.69000
• Density: 1.374±0.06 g/cm3(Predicted)
• LogP: 4.58660
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 568.24097336
• Heavy Atom Count: 41
• Complexity: 874

Purity/Quality:

98% min ^*data from raw suppliers

WS6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCN(CC1)CC2=C(C=C(C=C2)NC(=O)CC3=CC=C(C=C3)OC4=NC=NC(=C4)NC(=O)C5CC5)C(F)(F)F
• Uses: WS6 is a β-cell proliferation indocer via the IκB kinase pathway and modulation of the Erb3 binding-protein. Potential treatment and cure for diabetes type I.

Technology Process of N-(6-(4-(2-((4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-2-oxoethyl)phenoxy)pyrimidin-4-yl)cyclopropanecarboxamide

There total 7 articles about N-(6-(4-(2-((4-((4-Methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-2-oxoethyl)phenoxy)pyrimidin-4-yl)cyclopropanecarboxamide 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: 52.0%

4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethylaniline (694499-26-8) + 2-(4-(6-(cyclopropanecarboxamido)pyrimidin-4-yloxy)phenyl)acetic acid (1421227-58-8) → N-(6-(4-(2-((4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-2-oxoethyl)phenoxy)pyrimidin-4-yl)cyclopropanecarboxamide (1421227-53-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 7h;

DOI:10.1021/ja309304m

Reference yield:

Methyl 4-hydroxyphenylacetate (14199-15-6) → N-(6-(4-(2-((4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-2-oxoethyl)phenoxy)pyrimidin-4-yl)cyclopropanecarboxamide (1421227-53-3)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / 70 °C

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

3: lithium hydroxide monohydrate; water / methanol; tetrahydrofuran / 0.5 h / 20 °C

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 7 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium hydroxide monohydrate; water; potassium carbonate; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja309304m

Reference yield:

methyl 2-(4-(6-chloropyrimidin-4-yloxy)phenyl)acetate (1246636-79-2) → N-(6-(4-(2-((4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-2-oxoethyl)phenoxy)pyrimidin-4-yl)cyclopropanecarboxamide (1421227-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

2: lithium hydroxide monohydrate; water / methanol; tetrahydrofuran / 0.5 h / 20 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 7 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium hydroxide monohydrate; water; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/ja309304m

upstream raw materials:

Methyl 4-hydroxyphenylacetate

methyl 2-(4-(6-chloropyrimidin-4-yloxy)phenyl)acetate

methyl 2-(4-(6-(cyclopropanecarboxamido)pyrimidin-4-yloxy)phenyl)acetate

4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethylaniline

Refernces