Triethylamine → HCID 67386178, compound

Participants

Reaction Steps

To a solution of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (80 mg, 0.17 mmol) in DMF (2.4 mL) was added triethylamine (73 μl, 0.52 mmol), 1-((R)-2-amino-2-cyclopropyl-acetyl)-azetidine-3-carbonitrile (31.2 mg, 0.17 mmol) and PyBOP (109 mg, 0.21 mmol) at room temperature. The reaction mixture was stirred for 16 h at the same temperature then poured into EtOAc (50 mL) and washed with water (4×50 mL). The organic extracts were dried (Na2SO4) and evaporated under vacuum. The crude residue was purified by column chromatography (SiO2, 23 g, Hex:EtOAc, 0% to 6:4, in 35 min) to afford 42 mg (39%) of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide.

Provenance & Evidence