To a stirred solution of (11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea (Example 9, 50 mg, 0.18 mmol) in DMF (1 mL) was added 2-bromomethylnaphthalene (38.8 mg, 0.18 mmol) in one portion. The reaction mixture was stirred at room temperature for 1 hr then heated at 60° C. for 2 hrs. After this time, the solvent was removed in vacuo to leave an oily residue which was triturated with diethyl ether to give a yellow-brown solid. The solid was dissolved in 5 mL of tetrahydrofuran: 5 mL diethyl ether and treated with saturated sodium bicarbonate (10 mL). The organic layer was separated, dried over magnesium sulfate and evaporated to give a yellow oil. The product was purified by chromatography on silica gel (2% methanol: 98% dichloromethane). H1 NMR (acetone d6) δ: 8.81 (bs, 1H), 7.92-7.85 (m, 4H), 7.61 (bs, 1H), 7.50-7.39 (m, 4H), 7.09-6.91 (m, 7H), 5.81 (s, 2H).
