1-Hydroxybenzotriazole → HCID 71286077, compound

Participants

Reaction Steps

In a 20 mL scintillation vial, 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (120 mg, 0.26 mmol), (R)-4-aminopentanenitrile trifluoroacetate (51 mg, 0.524 mmol), HBTU (129 mg, 0.341 mmol), HOBt (46 mg, 0.341 mmol) and DIPEA (169 mg, 1.31 mmol) were combined with DMF (1.8 ml) to give a light yellow solution. After stirring at room temperature overnight the reaction mixture was diluted with EtOAc (50 mL) and washed with sat NaHCO3 (3×25 mL) and H2O (3×25 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 4 g, 0% to 10% MeOH in DCM with 0.1% NH4OH) to provide 99 mg (70%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-3-cyano-1-methyl-propyl)-amide as an off-white solid. MS: (M+H)+=539.

Provenance & Evidence