Trifluoroacetic acid → HCID 54755497, compound

Participants

Reaction Steps

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-cyano-phenyl)-amide (113 mg, 0.26 mmol) in CH2Cl2 (2.6 mL) was added trifluoroacetic acid (1 mL). Stirred at room temperature for 2 h then neutralized with aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was dissolved in EtOH and NaOAc (0.7 g) was added. The reaction mixture was stirred at 60° C. overnight then cooled to room temperature and water and EtOAc were added. The aqueous layer was extracted with EtOAc and the combined organics were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (MeOH/CH2Cl2) to give 22 mg (28%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (3-cyano-phenyl)-amide. MS: (M+H)+=304; mp=272.0-274.0.

Provenance & Evidence