Dimethylformamide → N-(6-(3-(N,4-Dimethylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

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Reaction Conditions

Reaction Steps

To a round-bottomed flask was added N-(6-(3-(4-methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (from Example 1, Step 5) (0.027 g, 0.064 mmol), potassium carbonate (0.013 g, 0.096 mmol), DMF (1.0 mL) and iodomethane (0.0044 mL, 0.071 mmol). The mixture was stirred at 25° C. for 14 h, then poured into water and extracted with EtOAc (3×30 mL). The combined extracts were washed with water (2×50 mL) and brine (50 mL) then dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (0 to 3% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a light-yellow solid. MS (ESI positive ion) m/z: 436 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.92 (s, 1H), 8.27 (s, 1H), 8.07 (d, J=9.6 Hz, 1H), 7.97 (d, J=8.4 Hz, 1H), 7.75 (t, J=1.9 Hz, 1H), 7.70 (d, J=9.6 Hz, 1H), 7.52 (t, J=7.9 Hz, 1H), 7.39-7.47 (m, 4H), 7.23 (dd, J=8.0 Hz, 1.4 Hz, 1H), 3.20 (s, 3H), 2.41 (s, 3H), 2.12 (s, 3H).

Provenance & Evidence