N-Desmethyl sorafenib

Base Information

• Chemical Name: N-Desmethyl sorafenib
• CAS No.: 284461-74-1
• Molecular Formula: C20H14ClF3N4O3
• Molecular Weight: 450.804
• UNII: N4T1W2J64C
• DSSTox Substance ID: DTXSID101117356
• Wikidata: Q27284553
• Pharos Ligand ID: XQQ9H5BZM9YC
• ChEMBL ID: CHEMBL403732
• Mol file: 284461-74-1.mol

Synonyms:N-Desmethyl sorafenib;284461-74-1;Sorafenib metabolite M4;BAY-439007;CHEMBL403732;N4T1W2J64C;4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]pyridine-2-carboxamide;BAY 43-9007;BAY-43-9007;n-(4-chloro-3-(trifluoromethyl)phenyl)-n'-(4-(2-carbamoyl-4-pyridyloxy)phenyl)urea;2-Pyridinecarboxamide, 4-(4-((((4-chloro-3-(trifluoromethyl) phenyl)amino)carbonyl)amino)phenoxy)-;2-Pyridinecarboxamide, 4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-;2-Pyridinecarboxamide,4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-;UNII-N4T1W2J64C;SCHEMBL548133;DTXSID101117356;BDBM50375257;4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)picolinamide;F77591;Q27284553;4-(4-(3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)picolinamide?;N-[4-chloro-3-(trifluoromethyl)phenyl]-N'-{4-[2-carbamoyl-(4-pyridyloxy)]phenyl} urea;N-[4-chloro-3-(trifluoromethyl)phenyl]-N'-{4-[2-carbamoyl-(4-pyridyloxy)]phenyl}urea;N-[4-chloro-3-(trifluoromethyl)phenyl]N'-{4-[2-carbamoyl-(4-pyridyloxy)]phenyl}urea;4-[4-[[[[4-Chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-2-pyridinecarboxamide

Chemical Property of N-Desmethyl sorafenib

Chemical Property:

• Boiling Point: 507.0±50.0 °C(Predicted)
• PKA: 12.90±0.70(Predicted)
• PSA: 106.34000
• Density: 1.513±0.06 g/cm3(Predicted)
• LogP: 6.13530
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 450.0706525
• Heavy Atom Count: 31
• Complexity: 631

Purity/Quality:

> 95% ^*data from raw suppliers

N-DesmethylSorafenib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1NC(=O)NC2=CC(=C(C=C2)Cl)C(F)(F)F)OC3=CC(=NC=C3)C(=O)N
• Uses: N-Desmethyl Sorafenib is a metabolite of Sorafenib (S676850) and has anti-proliferative activity in human breast cancer cells.

Technology Process of N-Desmethyl sorafenib

There total 12 articles about N-Desmethyl sorafenib 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: 96.2%

methyl 4‐(4‐(3‐(4‐chloro‐3‐(trifluoromethyl)phenyl)ureido)phenoxy)picolinate (573673-43-5) → 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-2-pyridine carboxamide (284461-74-1)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 6h;

Reference yield: 82.0%

4-(4-aminophenoxy)-2-pyridinecarboxamide (284462-80-2) + 4-chloro-3-trifluoromethyl-aniline (320-51-4) + 1,1'-carbonyldiimidazole (530-62-1) → 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-2-pyridine carboxamide (284461-74-1)

Guidance literature:

In tetrahydrofuran; methanol; 1,1-dichloroethane; ethyl acetate;

Reference yield: 82.0%

4-(4-aminophenoxy)-2-pyridinecarboxamide (284462-80-2) → 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-2-pyridine carboxamide (284461-74-1)

Guidance literature:

4-chloro-3-trifluoromethyl-aniline; With 1,1'-carbonyldiimidazole; In 1,1-dichloroethane; at 65 ℃; for 16h;

4-(4-aminophenoxy)-2-pyridinecarboxamide; In tetrahydrofuran; 1,1-dichloroethane; at 20 - 60 ℃; for 4h;

upstream raw materials:

4-(4-aminophenoxy)-2-pyridinecarboxamide

4-chloro-3-trifluoromethyl-aniline

1,1'-carbonyldiimidazole

methyl 4‐(4‐(3‐(4‐chloro‐3‐(trifluoromethyl)phenyl)ureido)phenoxy)picolinate

Downstream raw materials:

1-(4-(2-(aminomethyl)pyridin-4-yloxy)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea

BAY 68-7769