Water → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-ethoxythieno[2,3-b]pyrazine-6-carboxamide

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Reaction Steps

To a solution of N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 5 (38 mg, 0.132 mmol) and triethylamine (0.092 mL, 0.66 mmol) in CH2Cl2 (1 mL) was added 2-ethoxythieno[2,3-b]pyrazine-6-carbonyl chloride (32 mg, 0.132 mmol) in CH2Cl2 (1 mL) and stirred overnight at rt. Water was added and extracted with CH2Cl2. Organic layer was washed with water, dried and evaporated. Purification by HPLC gave N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-ethoxythieno[2,3-b]pyrazine-6-carboxamide (5 mg, 7%). 1H-NMR (400 MHz, DMSO-d6). 1.42 (t, J=7.0 Hz, 3H), 1.76 (s, 6H), 2.26 (s, 3H), 4.46 (q, J=7.0 Hz and 14.0 Hz, 2H), 7.31 (d, 8.2 Hz, 1H), 7.58-7.66 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.87 (d, J=1.9 Hz, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.05 (s, 1H), 8.35 (s, 1H), 8.41 (s, 1H), 10.35 (s, 1H), 10.37 (s, 1H). (m/z)=500 (M+H)+.

Provenance & Evidence