N,N-Dimethylethylenediamine → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-(dimethylamino)ethylamino)thieno[2,3-b]pyrazine-6-carboxamide

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Preparation analogous to 96a by using 3-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 95 (0.061 mmol, 30 mg) and 1-amino-2-dimethylaminoethane (1.531 mmol, 167 μL, 135 mg) to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-(dimethylamino)ethylamino)thieno[2,3-b]pyrazine-6-carboxamide 96c (12 mg, 36%). NMR (400 MHz, DMSO-d6) 1.75 (s, 6H), 2.22 (s, 6H), 2.24 (s, 3H), 3.45 (q, J=5.9 Hz, 2H), 7.28 (d, J=8.2 Hz, 1H), 7.61 (m, 2H), 7.75 (m, 2H), 7.82 (d, J=2.0 Hz, 1H), 7.95 (d, J=7.4 Hz, 1H), 8.05 (s, 1H), 8.19 (s, 1H), 8.24 (s, 1H), 10.07 (s, 1H), 10.33 (s, 1H). (m/z)=542 (M+H)+.

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