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

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,6-dibromopyrazine-2-carbonitrile 15 (286 mg, 1.089 mmol) and 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetamido)-4-methylphenyl)benzamide 16 (400 mg, 1.089 mmol) in ethanol (5 mL) was added potassium carbonate (211 mg, 1.524 mmol). The reaction was stirred 1 h at rt and 2 h at 50° C. Quenched in cooled 1N HCl solution (aq), the resulting precipitate was collected and dried to give crude compound 17 (588 mg). Purification by chromatography (0-10% EtOAc in CH2Cl2) gave pure 7-amino-2-bromo-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 17 (463 mg, 77%). 1H-NMR (400 MHz, DMSO-d6) 1.75 (s, 6H), 2.21 (s, 3H), 7.09 (br s, 2H), 7.27 (d, J=8.6 Hz, 1H), 7.60 (t, J=7.8 Hz, 2H), 7.75 (d, J=7.8 Hz, 1H), 7.81 (br s, 1H), 7.95 (d, J=7.0, 1H), 8.05 (s, 1H), 8.93 (br s, 1H), 9.58 (br s, 1H), 10.32 (br s, 1H). (m/z)=549 and 551 (M+H)+.

Provenance & Evidence