Hydrochloric Acid → 2-acetyl-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

Participants

Reaction Steps

A solution of 2-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 24 (50 mg, 0.102 mmol), bis(triphenylphosphine)palladium(ii) chloride (7.16 mg, 10.2 μmol) and 1-ethoxyvinyltri-n-butyltin (0.103 mL, 0.306 mmol) toluene (3 mL) was stirred at 100° C. for 2 h. Cooled down to rt, 4N HCl in Dioxane (1 mL) was added and stirred for 1 h. Diluted with EtOAC, filtrated and evaporated. Purification by chromatography (0-10% EtOAc in CH2Cl2) gave the title compound 2-acetyl-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 25g (13 mg, 25.6%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.28 (s, 3H), 2.76 (s, 3H), 7.33 (d, J=8.2 Hz, 1H), 7.58-7.68 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.91 (d, J=1.9 Hz, 1H), 7.96 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 8.65 (s, 1H), 9.20 (s, 1H), 10.39 (s, 1H), 10.57 (s, 1H). (m/z)=498 (M+H)+.

Provenance & Evidence