Potassium Cyanide → HCID 178464926, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methanesulfonic acid trans-3-(1-{[2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-ethyl)-cyclobutyl ester (crude from step 1, 97 mg, 0.16 mmol) in DMSO (1.5 mL) at room temperature was added potassium cyanide (41 mg, 0.63 mmol) and 18-crown-6 (8 mg, 0.03 mmol). The reaction mixture was heated at 100° C. overnight then cooled to room temperature, quenched with water, and extracted with EtOAc (3×). The combined organics were washed with water (3×) and brine then dried over MgSO4 and concentrated. The residue was purified via chromatography with 20% to 50% EtOAc/hexanes to isolate 34 mg (40%) 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-cyano-cyclobutyl)-ethyl]-amide as a yellow foam.

Provenance & Evidence