Microtubule inhibitor 3

Base Information

• Chemical Name: Microtubule inhibitor 3
• CAS No.: 1236141-96-0
• Molecular Formula: C₂₆H₂₃FN₄O₃
• Molecular Weight: 458.492
• DSSTox Substance ID: DTXSID601104506
• Nikkaji Number: J2.800.944E
• ChEMBL ID: CHEMBL2048720
• Mol file: 1236141-96-0.mol

Synonyms:Microtubule inhibitor 3;SCHEMBL807167;CHEMBL2048720;KPU-133;DTXSID601104506;HY-147724;CS-0526754;(3Z,6Z)-3-[[5-(1,1-Dimethylethyl)-1H-imidazol-4-yl]methylene]-6-[[3-(4-fluorobenzoyl)phenyl]methylene]-2,5-piperazinedione;1236141-96-0

Chemical Property of Microtubule inhibitor 3

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 458.17541877
• Heavy Atom Count: 34
• Complexity: 870

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C1=C(N=CN1)C=C2C(=O)NC(=CC3=CC(=CC=C3)C(=O)C4=CC=C(C=C4)F)C(=O)N2
• Isomeric SMILES: CC(C)(C)C1=C(N=CN1)/C=C\2/C(=O)N/C(=C\C3=CC(=CC=C3)C(=O)C4=CC=C(C=C4)F)/C(=O)N2

Technology Process of Microtubule inhibitor 3

There total 11 articles about Microtubule inhibitor 3 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: 70.1%

3-(4-fluorophenyl)formylbenzaldehyde + 1-acetyl-3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-2,5-piperazinedione (714273-84-4) → (3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylene)-6-(3-(4-fluorobenzoyl)benzylidene)piperazine-2,5-dione (1236141-96-0)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 48h; Inert atmosphere; Darkness;

DOI:10.1016/j.bmc.2019.115186

Reference yield:

5-(tert-butyl)-1H-imidazole-4-carbaldehyde (714273-83-3) → (3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylene)-6-(3-(4-fluorobenzoyl)benzylidene)piperazine-2,5-dione (1236141-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

2.1: caesium carbonate; sodium sulfate / N,N-dimethyl-formamide / 24 h / 60 °C / Inert atmosphere

2.2: 2 h / -20 °C

With caesium carbonate; sodium sulfate; In N,N-dimethyl-formamide; 1.1: |Aldol Addition;

DOI:10.1016/j.bmc.2020.115435

Reference yield:

4-fluoro-N-methoxy-N-methylbenzamide (116332-54-8) → (3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylene)-6-(3-(4-fluorobenzoyl)benzylidene)piperazine-2,5-dione (1236141-96-0)

Guidance literature:

Multi-step reaction with 4 steps

1: n-butyllithium / tetrahydrofuran; hexane / Inert atmosphere

2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 2 h / 0 °C / Inert atmosphere

3: dipyridinium dichromate / dichloromethane / 2 h / 20 °C / Molecular sieve

4: caesium carbonate / N,N-dimethyl-formamide / 70 °C / Inert atmosphere

With dipyridinium dichromate; n-butyllithium; diisobutylaluminium hydride; caesium carbonate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2012.05.059

upstream raw materials:

1-acetyl-3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-2,5-piperazinedione

4-Fluorobenzoic acid

4-fluoro-N-methoxy-N-methylbenzamide

3-(1,3-dioxolan-2-yl)-phenylbromide