Methanol → 1-(6-Bromo-7-benzyloxy-2-benzothiazolyl)-3-ethyl-urea

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A mixture of 1-(6-bromo-7-hydroxy-2-benzothiazolyl)-3-ethyl-urea 6 (0.050 g, 0.16 mmol) and potassium carbonate (0.023 g, 0.17 mmol, 1.05 eq) in anhydrous DMF (1.6 mL) was stirred at about 20° C. for about 0.5 hour, and was cooled down to about 0° C. The reaction mixture was treated with benzyl bromide (0.019 mL, 0.16 mmol, 1.0 eq), and was stirred at about 0° C. for about 16 hours. To the reaction mixture was added methanol (10 mL). The solid was filtered off and rinsed with methanol (3 mL). The solvent was evaporated and the residue was dissolved in DMF (2 mL). The crude reaction solution was purified by LC/MS to give 0.029 g (45%) of the desired compound 9. 1H NMR (DMSO) δ 10.86 (br s, 1H, NH), 7.59–7.34 (m, 7H, ArH), 6.72 (br s, 1H, NH), 5.17 (s, 2H, CH2), 3.18 (m, 2H, CH2), 1.09 (t, 3H, J=7.2 Hz, CH3); LC/MS 406 (MH+); RP-HPLC RT 3.8 minutes.

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