N-desethyl sunitinib

Base Information

• Chemical Name: N-desethyl sunitinib
• CAS No.: 356069-16-4
• Molecular Formula: C₂₀H₂₃FN₄O₂
• Molecular Weight: 370.427
• Mol file: 356069-16-4.mol

Synonyms:

Chemical Property of N-desethyl sunitinib

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-desethyl sunitinib

There total 7 articles about N-desethyl sunitinib 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: 74.0%

N-ethylethane-1,2-diamine (110-72-5) + 5-((5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (452105-33-8) → N-desethyl sunitinib (356069-16-4,356068-97-8)

Guidance literature:

5-((5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

N-ethylethane-1,2-diamine; In N,N-dimethyl-formamide; at -60 - 20 ℃; for 24h;

DOI:10.1002/jlcr.1608

Reference yield:

C25H31FN4O4 → N-desethyl sunitinib (356069-16-4,356068-97-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1158/0008-5472.CAN-15-2138

Reference yield:

2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester (2199-51-1) → N-desethyl sunitinib (356069-16-4,356068-97-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trichlorophosphate / dichloromethane / 1.25 h / 4 °C / Reflux

1.2: 10 °C

2.1: potassium hydroxide / water / 5 h / Reflux

2.2: pH 4

3.1: pyrrolidine / ethanol / 3 h / Reflux

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C

4.2: 24 h / -60 - 20 °C

With pyrrolidine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium hydroxide; trichlorophosphate; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/jlcr.1608

upstream raw materials:

N-ethylethane-1,2-diamine

5-((5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Refernces

• 1、 Argyros, Orestis,Karampelas, Theodoros,Asvos, Xenophon,Varela, Aimilia,Sayyad, Nisar,Papakyriakou, Athanasios,Davos, Constantinos H.,Tzakos, Andreas G.,Fokas, Demosthenes,Tamvakopoulos, Constantin. "Peptide-Drug conjugate gnrh-sunitinib targets angiogenesis selectively at the site of action to inhibit tumor growth". . p. 1181 - 1192. Retrieved 2016/04/05.