ESI(+) HPLC-MS analysis of the crude product solution obtained by reaction of precursor 8 with methyl triflate. (A) Calculated m/z values for the different main products and the derived benzothiazol fragments. (B) Total ion current (TIC) chromatogram filtered to m/z 407, which corresponds to tozadenant (tR = 10.4 min) and its regioisomers (tR = 7.6 and 11.2 min). (C) TIC filtered to m/z 292, which corresponds to the methylated benzothiazol fragment expected for tozadenant and its N-methylated regioisomer. The peak at 6.5 min (m/z = 421) corresponds to a product formed by double methylation and is therefore not relevant for no-carrier-added 11C-methylation reactions. HPLC conditions: Column: Phenomenex Kinetex® F5, 5 µm, 250 × 4.6 mm; eluent: 25% MeCN in H2O + 0.2% HCOOH, flow rate: 1.5 mL/min.