Potassium Carbonate → N-(4-(4-{5-(2-(Dimethylamino)ethoxy)pyrazin-2-ylthio}-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide

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Reaction Conditions

Reaction Steps

A mixture of N-(4-(4-iodo-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide (0.51 g, 1.2 mmol), 5-(2-(dimethylamino)ethoxy)pyrazine-2-thiol (28-4, 0.96 g, 4.8 mmol), copper iodide (73.0 mg, 0.38 mmol), and potassium carbonate (0.64 g, 4.6 mmol) in 5.0 mL of DMF was heated at 100° C. for 16 h. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (MeOH:CH2Cl2=1:10 as eluant) to give N-(4-(4-{5-(2-(dimethylamino)ethoxy)pyrazin-2-ylthio}-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide (28, 0.28 g) as light yellow solids in 47% yield: 1H NMR (500 MHz, CD3OD) δ 8.75 (s, 2 H), 8.14 (d, J=1.1 Hz, 1 H), 8.04 (s, 1 H), 7.97 (d, J=5.9 Hz, 2 H), 7.18 (s, 2 H), 7.00 (s, 1 H), 4.58 (s, 3 H), 4.46 (t, J=5.5 Hz, 2 H), 2.81 (t, J=5.4 Hz, 2 H), 2.37 (s, 6 H), 2.10 (s, 6 H). ESI-MS: m/z 507.1 (M+H)+.

Provenance & Evidence