Hydrochloric Acid → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate (0.24 g, 0.546 mmol), KOH (0.611 g, 10.9 mmol), water (4 mL) and dioxane (10 mL) was stirred at 100° C. for 5 hours. Then the reaction mixture was cooled to room temperature and treated with 1N HCl to pH=2. The solvent was evaporated at 40° C. under reduced pressure and the residue was triturated with water (10 mL), then decanted and dried at 40° C. under reduced pressure to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(pivaloyloxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.161 g, 94.8%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 12.87 (s, 1H), 12.28 (s, 1H), 9.05 (s, 1H), 8.82 (dd, 1H, J1=9.0 Hz, J2=5.7 Hz), 8.48 (d, 1H, J=2.7 Hz), 7.61 (dd, 1H, J1=10.2 Hz, J2=2.7 Hz), 7.15 (t, 1H, J=12.0 Hz), 4.12 (s, 3H). LCMS: 312.0 [M+H]+, 334.0 [M+Na]+.

Provenance & Evidence