Hydrochloric Acid → 4-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide

Participants

Reaction Steps

To a solution of 4-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-5-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide (142 mg, 0.261 mmol) in MeOH (2 mL) was added a 4M HCl solution in dioxane (2 mL). The reaction mixture was stirred at room temperature for 2 hours before being concentrated in vacuo. The resultant residue was taken up in ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate, water then brine, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was triturated in ethyl acetate/cyclohexane to afford the title compound as a solid (73 mg, 56%). LCMS (method A): RT=8.97 min, [M+H]+=504. NMR (DMSO-d6, 400 MHz) 11.78 (1 H, s), 9.28 (1 H, s), 8.64 (1 H, s), 7.84 (1 H, dd, J=8.48, 0.92 Hz), 7.64-7.57 (2 H, m), 7.31 (1 H, dd, J=8.47, 1.83 Hz), 6.65 (1 H, t, J=8.71 Hz), 4.80 (1 H, s), 4.54 (1 H, s), 3.80 (1 H, t, J=6.46 Hz), 3.68-3.61 (2 H, m), 3.32 (2 H, s).

Provenance & Evidence