Bromobutene linagliptin impurity VII is a synthetic byproduct arising from the bromination of a butene moiety during linagliptin API synthesis. It features a brominated conjugated butene backbone linked to a substituted pyrazine-triazole heterocyclic core, with an N-acylated sulfonamide side chain. The compound retains key pharmacophoric elements of linagliptin but incorporates a bromide substituent at the ฮฒ-position of the butenyl bridge, inducing steric and electronic deviations from the parent drug. This impurity serves as an HPLC reference standard for quantifying process-related deviations in linagliptin manufacturing.
On RequestCC1=NC(=NC2=CC=CC=C12)CN3C(=O)C4=C(N=C(N4C/C=C(\C)/Br)N5CCC[C@H](C5)N)N(C3=O)C
InChI=1S/C25H29BrN8O2/c1-15(26)10-12-33-21-22(30-24(33)32-11-6-7-17(27)13-32)31(3)25(36)34(23(21)35)14-20-28-16(2)18-8-4-5-9-19(18)29-20/h4-5,8-10,17H,6-7,11-14,27H2,1-3H3/b15-10+/t17-/m1/s1
KOVUTSTYXMWMHQ-IUYQLWOBSA-N