Pyrrolidine → N-(2-methyl-5-(2-(pyrrolidin-1-yl)isonicotinamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(5-(2-bromoisonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 30 (25 mg, 0.053 mmol) in pyrrolidine (0.5 mL) was heated at 80° C. overnight. Quenched in 3% citric acid solution and extracted with CH2Cl2 (2×). The combined organic layers were dried with Na2SO4 and concentrated in vacuo. Purification by chromatography CH2Cl2/MeOH (97/3) and triturating with acetonitrile gave the title compound N-(2-methyl-5-(2-(pyrrolidin-1-yl)isonicotinamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide 31b (10.7 mg, 44%). NMR (400 MHz, DMSO-d6) 1.97 (m, 4H), 2.26 (s, 3H), 3.45 (m, 4H), 6.88 (s, 1H), 6.98 (dd, J=5.1 and 1.2 Hz, 1H), 7.30 (d, J=8.6 Hz, 1H), 7.62 (dd, J=8.23 and 1.6 Hz, 1H), 7.87 (d, J=2.3 Hz, 1H), 8.21 (d, J=5.1 Hz, 1H), 8.53 (br s, 1H), 8.75 (d, J=2.3 Hz, 1H), 8.88 (d, J=2.3 Hz, 1H), 10.33 (s, 1H), 10.52 (s, 1H). (m/z)=459 (M+H)+.

Provenance & Evidence