Dimethylformamide → HCID 178426563, compound

Participants

Reaction Steps

A solution of 7-aminothieno[2,3-b]pyrazine-6-carboxylic acid 8 (33.8 mg, 0.179 mmol), HATU (74.1 mg, 0.195 mmol), DIPEA (0.081 mL, 0.488 mmol) in DMF (1 mL) was stirred at rt for 30 min. 2-(5-amino-2-methylphenylamino)-2-(thieno[2,3-b]pyrazin-6-yl)acetonitrile 78 (48 mg, 0.163 mmol) was added and stirred overnight at rt. Quenched with citric acid solution (3%) and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated. Purification by HPLC gave the title compound (E)-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carbimidoyl cyanide 79 (4 mg, 5.30%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.26 (s, 3H), 7.41 (d, J=8.2 Hz, 1H), 7.63 (m, 2H), 7.77 (m, 1H), 7.86 (d, J=2.0 Hz, 1H), 7.97 (d, J=7.4 Hz, 1H), 8.06 (s, 1H), 8.36 (s, 1H), 8.80 (d, J=2.3 Hz, 1H), 8.93 (d, J=2.3 Hz, 1H), 10.49 (s, 1H). (m/z)=465 (M+H)+.

Provenance & Evidence