Mirabegron Impurity 5 is a synthetic byproduct arising from the oxidation of a sulfide intermediate during the final stages of Mirabegron synthesis. It features a substituted benzamide core linked to a piperazine ring, with a key structural distinction being the presence of a sulfonyl group (โSO2โ) in place of the parent compound's sulfide moiety. This impurity retains the ฮฒ-adrenergic agonist scaffold but exhibits altered electronic properties due to the sulfonyl oxygen's electron-withdrawing effect. It serves as a critical HPLC reference standard for quantifying process-related impurities in Mirabegron drug substance batches.
On RequestC1=C(N=C(S1)N)CC(=O)NC2=NC(=CS2)CC(=O)O
InChI=1S/C10H10N4O3S2/c11-9-12-5(3-18-9)1-7(15)14-10-13-6(4-19-10)2-8(16)17/h3-4H,1-2H2,(H2,11,12)(H,16,17)(H,13,14,15)
BWQNIGDPLBVJBJ-UHFFFAOYSA-N