Trifluoroacetic acid → HCID 58438546, compound

Participants

Reaction Steps

To a solution of 2-(1-cyclopropylmethyl-1H-imidazol-4-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide (160 mg, 0.26 mmol) in CH2Cl2 (2.25 mL) was added trifluoroacetic acid (0.75 mL). The reaction mixture was stirred at room temperature for 2 h and concentrated. The residue was dissolved in a mixture of ammonium hydroxide, MeOH and CH2Cl2 (1:10:60, 3.0 mL) and stirred at room temperature for 30 min. The reaction mixture was then concentrated and the residue purified twice by SiO2 chromatography (0-5% MeOH/EtOAc then 0-10% MeOH/CH2Cl2) to afford 27 mg (21%) of 2-(1-cyclopropylmethyl-1H-imidazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyano-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide as a white powder. MS: (M+H)+=489.

Provenance & Evidence