Diisopropylethylamine → HCID 178464928, compound

Participants

Reaction Steps

To a solution of cis-3-(1-aminoethyl)-cyclobutanol hydrochloride (crude from step 6, 91 mg, 0.60 mmol) in DMF (2 mL) were added N,N-diisopropylethylamine (0.24 mL, 1.36 mmol), 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (120 mg, 0.27 mmol), and HATU (114 mg, 0.30 mmol). The yellow reaction mixture was stirred at room temperature overnight then quenched with water and extracted with EtOAc (3×). The combined organics were washed with water (3×) and brine then dried over MgSO4 and concentrated to a pale yellow solid. Trituration with EtOAc/Et2O gave 108 mg (74%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(cis-3-hydroxy-cyclobutyl)-ethyl]-amide as a white solid.

Provenance & Evidence