Ethanolamine → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-hydroxyethylamino)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 2-aminoethanol (1.53 mmol, 92 μL). The crude compound was purified by HPLC and the chromatography (0-10 methanol in CH2Cl2) to give N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(2-hydroxyethylamino)thieno[2,3-b]pyrazine-6-carboxamide 96h (5 mg, 15%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.24 (s, 3H), 3.44 (q, J=5.9 Hz and 5.1 Hz, 2H), 3.59 (q, J=5.9 Hz and 5.1 Hz, 2H), 4.83 (t, J=5.1 Hz, 1H), 7.28 (d, J=8.6 Hz, 1H), 7.60 (m, 2H), 7.75 (m, 1H), 7.83 (d, J=2.0 Hz, 1H), 7.89 (m, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.05 (s, 1H), 8.17 (s, 1H), 8.25 (s, 1H), 10.08 (s, 1H), 10.34 (s, 1H). (m/z)=516 (M+H)+.

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