C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([CH2:11][CH3:12])[CH2:9][CH3:10].[I-].[Na+].[O:15]=[S:16]1(=[O:33])[CH2:21][CH2:20][N:19]2[CH:22]=[CH:23][CH:24]=[C:25]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[C:18]2=[N:17]1.[OH-].[Na+]>CS(C)=O>[CH2:9]([CH:8]([O:32][C:29]1[CH:28]=[CH:27][C:26]([C:25]2[C:18]3=[N:17][S:16](=[O:33])(=[O:15])[CH2:21][CH2:20][N:19]3[CH:22]=[CH:23][CH:24]=2)=[CH:31][CH:30]=1)[CH2:11][CH3:12])[CH3:10]A mixture of potassium carbonate (750 mg), 3-bromopentane (820 mg), sodium iodide (814 mg) and 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (300 mg) in DMSO (5 mL) was stirred at 150° C. for 3 hr. The mixture was poured into 1N NaOH aq. and extracted with EtOAc. The organic layer was separated, washed with 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) to give a solid. This material was purified by preparative HPLC (C18, eluted with H2O in acetonitrile containing 0.1% TFA). The desired fraction was neutralized with sat.NaHCO3 aq. and extracted with EtOAc. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (36.1 mg) as a pale yellow solid.
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