Hydrochloric Acid → 7-(4-Bromo-2-fluoro-phenylamino)-benzo[d]isothiazole-6-carboxylic acid (2-hydroxy-ethoxy)-amide

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Reaction Steps

To a solution of 7-(4-bromo-2-fluoro-phenylamino)-benzo[d]isothiazole-6-carboxylic acid (2-vinyloxy-ethoxy)-amide (95 mg, 0.21 mmol) in MeOH (4 mL) was added a 1.0M aqueous solution of hydrochloric acid (0.42 mL). The reaction mixture was stirred at room temperature for 1 hour before being concentrated in vacuo. The resultant residue was taken up in ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate then brine, dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0% to 100%, ethyl acetate in DCM) to afford the title compound as a yellow solid (62 mg, 70%). LCMS (method A): RT=9.51 min, [M+H]+=426/428. 1H NMR (CDCl3, 400 MHz) 9.37 (1 H, s), 8.85 (1 H, s), 8.76 (1 H, s), 7.51 (1 H, d, J=8.40 Hz), 7.43 (1 H, d, J=8.40 Hz), 7.34-7.29 (1 H, m), 7.28 (1 H, d, J=8.75 Hz), 7.02 (1 H, t, J=8.46 Hz), 4.10 (2 H, t, J=4.09 Hz), 3.91 (1 H, s), 3.80 (2 H, s).

Provenance & Evidence