Hydrochloric Acid → 5-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-hydroxyethoxy)-amide

Participants

Reaction Steps

To a suspension of 5-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2-vinyloxyethoxy)-amide (1.33 g, 3.05 mmol) in methanol (40 mL) was added aqueous hydrochloric acid (6.7 mL, 1M, 6.7 mmol). The reaction mixture was stirred at room temperature for 30 minutes then concentrated in vacuo to remove the methanol. The resultant residue was dissolved in 1:1 diethylether:ethyl acetate (30 mL) and aqueous saturated sodium hydrogen carbonate solution (30 mL) added. The resultant mixture was sonicated until a precipitate formed, the precipitate collected by filtration and washed with water then diethyl ether to yield the title compound as a yellow solid (1.12 g, 90%). LCMS (method A): RT=5.22 min, [M+H]+=409/411. 1H NMR (DMSO-d6, 400 MHz) 9.20 (1 H, s), 8.07 (1 H, s), 7.51 (1 H, dd, J=10.86, 2.22 Hz), 7.44 (1 H, s), 7.40 (1 H, d, J=9.33 Hz), 7.16 (1 H, ddd, J=8.61, 2.20, 1.07 Hz), 6.89 (1 H, d, J=9.31 Hz), 6.50 (1H, t, J=8.84 Hz), 4.63 (1 H, s), 3.65 (2 H, t, J=4.79 Hz), 3.46 (3 H, s).

Provenance & Evidence