Potassium Carbonate → 7-amino-2-cyano-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

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Reaction Steps

A solution of 3-bromopyrazine-2,6-dicarbonitrile 52 (17.06 mg, 0.082 mmol), 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamide 16 (0.082 mmol, 30 mg) and potassium carbonate (13.54 mg, 0.098 mmol) in ethanol (1 mL) was stirred at 40° C. for 1 h. Quenched in 2N HCl solution and extracted with CH2Cl2. Organic layer was washed with brine, dried and evaporated. Purification by chromatography (5-10% EtOAc in CH2Cl2) gave the title compound 7-amino-2-cyano-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 53 (6 mg, 14.83%). NMR (400 MHz, DMSO-d6) 1.75 (s, 6H), 2.22 (s, 3H), 7.29 (m, 2H), 7.60 (t, J=7.8 Hz, 2H), 7.75 (m, 1H), 7.81 (d, 2.0 Hz, 1H), 7.94 (d, J=Hz, J=7.8 Hz, 1H), 8.05 (t, J=2.0 Hz, 1H), 9.65 (s, 1H), 10.34 (s, 1H). (m/z)=496 (M+H)+.

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