[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1[OH:17].[Br:18]Br.C1(C)C=CC=CC=1>CC(O)=O>[Br:18][C:15]1[C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]([OH:17])=[C:2]([Br:1])[CH:16]=1To a suspension of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea (50 mg, 0.158 mmol) in AcOH (2 mL) at about 20° C. was added Br2 (9 μl, 0.174 mmol). The reaction mixture was stirred at about 20° C. for about 15 minutes. Toluene (10 mL) was added and the solvents evaporated. The crude material was purified by preparative LC/MS to give 19 mg (30%) pure 18. 1H NMR (DMSO) δ 1.09 (t, 3H, J=6 Hz CH3), 3.19 (m, 2H, CH2), 6.55 (br s, 1H, NH), 7.68 (s, 1H, ArH), 10.51 (br s, 1H, NH or OH), 11.20 (br s, 1H, NH or OH). HPLC retention timer 2.90 minutes.
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