Diisopropylethylamine → N-(3-(5-Cyanopyrazin-2-ylamino)isoquinolin-8-yl)-3-methoxypropanamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(8-aminoisoquinolin-3-ylamino)pyrazine-2-carbonitrile (36 mg, 0.14 mmol), 3-methoxypropionic acid (34 mg, 0.32 mmol), N-hydroxybenzotriazole hydrate (64 mg, 0.42 mmol) and diisopropylethylamine (78 mg, 0.60 mmol) in DMF (1 mL), was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (78 mg, 0.42 mmol). The reaction mixture was stirred at 40° C. for 48 hours and then concentrated to dryness. Preparative HPLC gave the title compound (5.7 mg, 0.016 mmol, 12%). 1H NMR (d6-DMSO, 400 MHz) δ 11.05 (br s, 1H), 10.20 (s, 1H), 9.32 (s, 1H), 8.82 (d, 1H, J=1.2 Hz), 8.71 (d, 1H, J=1.2 Hz), 8.49 (s, 1H), 7.65-7.75 (m, 3H), 3.71 (t, 2H, J=6.1 Hz), 3.32 (s, 3H, obscured by water signal), 2.75 (t, 2H, J=6.1 Hz). LC-MS (2) Rt=2.10 min; m/z (ESI+) 349 (M+H).

Provenance & Evidence