N-Desmethyl vandetanib

Base Information

• Chemical Name: N-Desmethyl vandetanib
• CAS No.: 338992-12-4
• Molecular Formula: C21H22BrFN4O2
• Molecular Weight: 461.334
• UNII: K4I43R5TNP
• DSSTox Substance ID: DTXSID50416177
• Nikkaji Number: J1.720.299E
• Wikidata: Q27281946
• Mol file: 338992-12-4.mol

Synonyms:N-Desmethyl vandetanib;N-Demethyl Vandetanib;338992-12-4;N-(4-bromo-2-fluorophenyl)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazolin-4-amine;N-Desmethylvandetanib;N-Desmethyl-ZD6474;K4I43R5TNP;N-Desmethyl metabolite of vandetanib;UNII-K4I43R5TNP;J1.720.299E;M382558;4-(4-Bromo-2-fluoroanilino)-6-methoxy-7-((piperidin-4-yl)methoxy)quinazoline;4-Quinazolinamine, N-(4-bromo-2-fluorophenyl)-6-methoxy-7-(4-piperidinylmethoxy)-;4-Anilinoquinazoline 22;BDBM4675;SCHEMBL1612820;DTXSID50416177;HTCPERSEGREUFC-UHFFFAOYSA-N;FT-0665752;Q-101403;Q27281946;4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline;7-(4-Piperidinylmethoxy)-6-methoxy-4-(2-fluoro-4-bromoanilino)quinazoline;N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(piperidin-4-yl)methoxy]quinazolin-4-amine

Chemical Property of N-Desmethyl vandetanib

Chemical Property:

• PSA: 68.30000
• LogP: 5.06380
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 460.09102
• Heavy Atom Count: 29
• Complexity: 513

Purity/Quality:

99% ^*data from raw suppliers

N-DemethylVandetanib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=NC=N2)NC3=C(C=C(C=C3)Br)F)OCC4CCNCC4
• Uses: A major metabolite of Vandetanib (V097100).

Technology Process of N-Desmethyl vandetanib

There total 14 articles about N-Desmethyl vandetanib 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: 83.0%

4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester (338992-20-4) → N-Desmethylvandetanib (338992-12-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2017.02.082

Reference yield:

N-tert-butoxycarbonyl-4-(4-toluenesulphonyloxymethyl)piperidine (166815-96-9) → N-Desmethylvandetanib (338992-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / K₂CO₃ / dimethylformamide / 2 h / 95 °C

2: 70 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With potassium carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011022e

Reference yield:

4-(4-bromo-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline (196603-96-0) → N-Desmethylvandetanib (338992-12-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / K₂CO₃ / dimethylformamide / 2 h / 95 °C

2: 70 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With potassium carbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011022e

upstream raw materials:

4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)piperidine-1-carboxylic acid tert-butyl ester

N-tert-butoxycarbonyl-4-(4-toluenesulphonyloxymethyl)piperidine

4-(4-bromo-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

4-bromo-2-fluoroaniline

Downstream raw materials:

N-(4-bromo-2-fluorophenyl)-6-methoxy-7-((1-[11C]methylpiperidin-4-yl)methoxy)quinazolin-4-amine

4-((4-bromo-2-fluorophenyl)amino)-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-6-ol

vandetanib

N-(4-bromo-2-fluorophenyl)-6-methoxy-7-((1-d3-methyl-piperidin-4-yl)methoxy)quinazolin-4-amine

Refernces

• 1、 Gao, Mingzhang,Lola, Christian M.,Wang, Min,Miller, Kathy D.,Sledge, George W.,Zheng, Qi-Huang. "Radiosynthesis of [11C]Vandetanib and [11C]chloro- Vandetanib as new potential PET agents for imaging of VEGFR in cancer". experimental part. p. 3222 - 3226. Retrieved 2011/07/07.
• 2、 -. "QUINAZOLINE DERIVATIVES AS VEGF INHIBITORS". Page/Page column 18. . Retrieved 2010/11/08.