Dimethylamine, hydrochloride → N-(5-(2-(dimethylamino)isonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(5-(2-bromoisonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 30 (25 mg, 0.053 mmol) in ethanol (1 mL) was added dimethylamine HCl (24.07 mg, 0.534 mmol) and TEA (10 eq). The resulting mixture was heated at 80° C. overnight and 2 h at 150° C. in microwave. Quenched in 3% citric acid solution and extracted with CH2Cl2 (2×). The combined organic layers were dried with Na2SO4 and evaporated. Triturating with ethyl acetate/heptane gave the title compound N-(5-(2-(dimethylamino)isonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 31a (11.3 mg, 49%). NMR (400 MHz, DMSO-d6) 2.26 (s, 3H), 3.11 (s, 6H), 7.03 (d, J=5.1 Hz, 1H), 7.10 (br s, 1H), 7.31 (d, J=8.2 Hz, 1H), 7.63 (dd, J=8.2 and 1.9 Hz, 1H), 7.87 (d, J=1.9 Hz, 1H), 8.23 (d, J=5.1 Hz, 1H), 8.56 (br s, 1H), 8.76 (d, J=2.3 Hz, 1H), 8.89 (d, J=2.3 Hz, 1H), 10.39 (br s, 1H), 10.54 (br s, 1H). (m/z)=433 (M+H)+.

Provenance & Evidence