Hydrogen Peroxide → 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-7-(4-morpholinyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine 4,4-dioxide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(1-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazin-7-yl)morpholine (40 mg, 0.084 mmol) in EtOAc (2.5 mL) was added disodium tungstate (24.8 mg, 0.084 mol) and water (0.3 mL). The reaction was cooled at 0° C. and then H2O2 (25.9 μL, 0.84 mmol, 30%) was added. The reaction was allowed to warm to rt for 1 h. After this time more disodium tungstate (7 mg) was added followed by H2O2 (0.4 mL, 30%) and the reaction was stirred at rt overnight. After this time the reaction was diluted with EtOAc (50 mL) and treated with a saturated aqueous solution of NaHSO3 (15 mL). The separated organic layer was washed with brine (15 mL), dried over MgSO4, filtered and evaporated in vacuo to give 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-7-(4-morpholinyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine 4,4-dioxide. 1H NMR (400 MHz, chloroform-d) δ ppm 8.64-8.81 (1H, m), 7.87-7.95 (4H, m), 7.74 (1H, dd, J=9.1, 5.8 Hz), 7.36-7.45 (2H, m), 5.59 (1H, s), 4.21-4.26 (2H, m), 3.63-3.72 (6H, m), 2.88-3.01 (4H, m), 2.46 (3H, s). Mass Spectrum (ESI) m/e=506.0 (M+1).

Provenance & Evidence