Potassium Carbonate → tert-Butyl (5-{[4-{[4-(difluoromethoxy)phenyl]amino}-1,1-dioxido-3-oxo-5-phenylisothiazol-2(3H)-yl]methyl}pyridin-2-yl)carbamate

Participants

Reaction Steps

[4-[Difluoromethoxy)phenyl]amine (0.27 g, 1.7 mmol) was added to an ice cold solution of 4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.41 g, 1.7 mmol) in DMF (4 ml) and the mixture was stirred for 1 h. tert-Butyl[5-(bromomethyl)pyridin-2-yl]carbamate (0.48 g, 1.7 mmol) and anhydrous potassium carbonate (0.23 g, 1.7 mmol) were added. The reaction mixture was stirred over night, concentrated and the residue was dissolved in DCM. The mixture was washed with water and concentrated and the residue was purified using preparative HPLC to give the title compound (0.12 g, 13%). 1H NMR (400 MHz, d6-DMSO): δ 1.41 (s, 9H), 3.77 (dd, 2H), 7.22-7.24 (m, 3H), 7.27 (t, 1H), 7.39-7.45 (m, 5H), 7.48 (d, 1H), 7.78 (d, 1H), 7.86 (dd, 2H), 9.57 (s, 1H), 11.18 (s, 1H); Mass Spectrum: M+H+ 573.

Provenance & Evidence