Sodium Bicarbonate → 3(2H)-Isothiazolone, 2-butyl-5-phenyl-4-[(1,2,3,4-tetrahydro-6-isoquinolinyl)amino]-, 1,1-dioxide

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Reaction Steps

A mixture of tert-butyl 6-[(2-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]-3,4-dihydroisoquinoline-2(1H)-carboxylate (example 24) (0.585 g, 1.144 mmol) in DCM (10 ml) and TFA (2 ml) was stirred at rt for 2.5 h. The reaction mixture was basified by addition of saturated aqueous NaHCO3. The organic phase was washed with saturated aqueous NaHCO3 and brine. The mixture was evaporated and the residue was purified by flash chromatography using 0-20% MeOH in DCM as eluent to give the title compound (0.315 g, 67%). 1H NMR (500 MHz DMSO-d6); δ 9.44 (bs, 1H), 7.26 (td, 1H), 7.19 (td, 2H), 7.05 (d, 2H), 6.76-6.68 (m, 3H), 6.29 (s, 1H), 3.78 (s, 2H), 3.69 (t, 2H), 2.86 (t, 2H), 2.27 (t, 3H), 1.78-1.68 (m, 2H), 1.46-1.36 (m, 2H), 0.93 (t, 3H); 13C NMR (125 MHz CDCl3): 159.5, 134.4, 134.3, 130.7, 129.6, 129.5, 128.3, 126.6, 125.4, 122.9, 119.9, 111.2, 46.9, 43.1, 40.5, 30.5, 28.1, 20.3, 13.8: Mass Spectrum: M+H+ 412.

Provenance & Evidence