Diisopropylethylamine → HCID 131735270, compound

Participants

Reaction Steps

To a solution of 1-((S)-2-amino-2-(tetrahydropyran-4-yl)acetyl)-N-(2,6-difluorophenyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (37 mg, 88.9 μmol, Eq: 1.00), (S)-2-(tert-butoxycarbonyl(methyl)amino)propanoic acid (27.1 mg, 133 μmol, Eq: 1.5) and diisopropyl-ethylamine (62 μL, 355 μmol, Eq: 4) in DMF was added HATU (60.8 mg, 160 μmol, Eq: 1.8) and the resulting solution was stirred at rt. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (10 mL). The organic layer was then washed with 0.1 M aqueous NaOH and brine and then concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 0% to 100% EtOAc in hexanes) to give tert-butyl (2S)-1-((1S)-2-(2-(2,6-difluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-2-oxo-1-(tetrahydro-2 h-pyran-4-yl)ethylamino)-1-oxopropan-2-yl(methyl)carbamate (54 mg), m/z=602 (M+H).

Provenance & Evidence