Chlorosulfonyl isocyanate → 2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine-7-carbonitrile

Participants

Reaction Steps

To a stirred solution of 2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine (from Example 1, Step 5, 50.0 mg, 10.9 μmol) in N,N-dimethylformamide (2 mL), chlorosulfonyl isocyanate (24.0 μL, 27.6 μmol) was added at 0° C. The reaction mixture was then warmed to ambient temperature and kept stirring overnight. The volatiles were removed and the residue was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min) to give the desired product (1.2 mg) as its TFA salt. LCMS calculated for C28H31N6O2 (M+H)+: m/z=483.2. Found: 483.2.

Provenance & Evidence