Hydrochloric Acid → HCID 44603271, compound

Participants

Reaction Steps

To a solution of 7-(2-fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-6-carboxylic acid (2-vinyloxy-ethoxy)-amide (187 mg, 0.37 mmol) in MeOH (4 mL) was added a 1.0M aqueous solution of hydrochloric acid (0.75 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 (128 mg, 72%). LCMS (method A): RT=9.81 min, [M+H]+=474. 1H NMR (CDCl3, 400 MHz) 9.33 (1 H, s), 8.86 (1 H, s), 8.77 (1 H, s), 7.55-7.40 (4 H, m), 6.84 (1 H, t, J=8.30 Hz), 4.10 (2 H, t, J=4.16 Hz), 3.91 (1 H, t, J=6.45 Hz), 3.80 (2 H, t, J=4.55 Hz).

Provenance & Evidence