Hydrochloric Acid → 4-[(2-Fluoro-4-Iodophenyl)amino]-N-(2-Hydroxyethoxy)-1h-Indazole-5-Carboxamide

Participants

Reaction Steps

To a solution of 4-(2-fluoro-4-iodophenylamino)-1H-indazole-5-carboxylic acid (2-vinyloxyethoxy)-amide (1.85 g, 3.84 mmol) in methanol (40 mL) was added hydrochloric acid (3 mL, 1N, 3 mmol). The reaction mixture was stirred at room temperature for 1 hour, during which an off-white solid precipitated. The reaction mixture was concentrated in vacuo and the residue triturated with hot methanol/water (10 mL, 1:1). The product was collected by filtration and dried in vacuo to yield the title compound as an off white solid (1.26 g, 72%). LCMS (Method A): RT=8.28 min, [M+H]+=457. 1H NMR (DMSO-d6): 13.20 (1 H, s), 11.61 (1 H, s), 9.93 (1 H, s), 7.66 (1 H, dd, J=10.32, 1.95 Hz), 7.46 (1 H, d, J=8.81 Hz), 7.42 (1 H, dd, J=8.49, 1.84 Hz), 7.24 (1 H, s), 7.01 (1 H, d, J=8.78 Hz), 6.91 (1 H, t, J=8.65 Hz), 4.68 (1 H, s), 3.85 (2 H, dd, J=5.41, 4.48 Hz), 3.56 (2 H, t, J=4.85 Hz).

Provenance & Evidence