284462-37-9Sorafenib Aminophenoxy Impurity

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Catalogue No.:	VE005959
CAS No.:	284462-37-9
Mol. Formula:	C13H13N3O2
Mol. Weight:	243.26 g/mol

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Additional information on CAS 284462-37-9

Parent drug

Sorafenib

IUPAC Name

4-(4-Aminophenoxy)-N-methylpyridine-2-carboxamide

Pharmacopeial Synonyms

Sorafenib EP Impurity A; Sorafenib Impurity A

Synonyms

4-(4-Aminophenoxy)-N-methylpicolinamide; 2-Pyridinecarboxamide, 4-(4-aminophenoxy)-N-methyl-

Smiles

O=C(NC)C1=NC=CC(OC2=CC=C(N)C=C2)=C1

InChI

InChI=1S/C13H13N3O2/c1-15-13(17)12-8-11(6-7-16-12)18-10-4-2-9(14)3-5-10/h2-8H,14H2,1H3,(H,15,17)

Description

Sorafenib Aminophenoxy Impurity, also designated Sorafenib EP Impurity A and Sorafenib Impurity A, CAS 284462-37-9, is the aniline-linked precursor 4-(4-aminophenoxy)-N-methylpicolinamide, formula C13H13N3O2, molecular weight 243.26 g/mol. Structurally it corresponds to an aryl ether intermediate associated with sorafenib synthesis, commonly arising from incomplete coupling or insufficient amination during route development. It is not a nitrosamine, but its presence is controlled as a process-related related substance under pharmacopoeial impurity profiling. Determination typically requires LC-MS/MS or high-resolution LC-MS, with orthogonal confirmation by HPLC-UV and, when needed, NMR characterization.

References

Johnsirani, P., et al. “LC-ESI-QTOF-MS Analysis Utilizing Gas-Phase Fragmentation Reactions Subjected to ESI-IS-CID and ESI-CID-MS/MS Conditions to Study the Degradation Behaviour of Sorafenib Tosylate: NMR and in Vitro Cytotoxicity and Apoptosis Detection Studies of Hydrolytic Degradation Products.” Journal of Pharmaceutical and Biomedical Analysis, vol. 177, Jan. 2020, p. 112881, https://doi.org/10.1016/j.jpba.2019.112881. ?