Methanol → HCID 178464929, compound

Participants

Reaction Steps

To a suspension of 4-nitrobenzoic acid trans-3-(1-{[2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-ethyl)-cyclobutyl ester (250 mg, 0.36 mmol) in THF (12 mL) was added 10% aqueous sodium hydroxide (0.44 mL, 1.09 mmol), water (1 mL), and MeOH (2 mL). The reaction mixture was stirred at room temperature for 30 min then diluted with water and extracted with CH2Cl2 (3×). The combined organics were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 30% to 80% EtOAc/hexanes to afford 140 mg (72%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(trans-3-hydroxy-cyclobutyl)-ethyl]-amide as an off-white solid.

Provenance & Evidence