Tetrahydrofuran → 1-(2,5-Dimethylbenzyl)-9-(quinoxalin-2-yl)-1,9-diazaspiro[5.5]undecan-2-one

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To a solution of 9-(quinoxalin-2-yl)-1,9-diazaspiro[5.5]undecan-2-one (80 mg, 0.27 mmol) in THF (5 mL) sodium hydride 95% (32 mg, 0.81 mmol) was added and the mixture was stirred for 10 min at rt. Then 2,5-dimethylbenzylchloride (70 mg, 0.35 mmol) was added and the reaction mixture was heated at 60° C. over 18 h. Saturated aqueous NH4Cl solution (40 mL) was added and the reaction mixture was extracted with ethyl acetate (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude product was purified by reversed phase preparative HPLC (column Zorbax eclipseXDB C18, flow 20 mL/min, mobile phase 0.1% TFA in water (A): acetonitrile (B) gradient) to yield the title compound (49 mg, 22%). [1H NMR (300 MHz, CDCl3) δ 8.55 (s, 1H), 7.88 (d, 1H), 7.70-7.55 (m, 2H), 7.48-7.35 (t, 1H), 7.05-6.85 (m, 2H), 6.72 (s, 1H), 4.55 (s, 2H), 4.55-4.39 (m, 2H), 3.12 (t, 2H), 2.65 (t, 2H), 2.30 (s, 3H), 2.15 (s, 3H), 2.20-1.88 (m, 6H), 1.85-1.63 (m, 2H); LCMS RtE=1.64 min, [M+H]+=415.2].

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