2-Morpholinoethylamine → HCID 10426742, compound

Participants

Reaction Steps

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.68 g, 3.5 mmol) was added in one portion to a stirred suspension of 2-morpholin-4-ylethanamine (0.422 g, 3.2 mmol), 3-amino-6-bromopyrazine-2-carboxylic acid (0.64 g, 3.0 mmol; described in: Ellingson, R. C.; Henry, R. L. J. Am. Chem. Soc. 1949, 2798-2800), and 1-hydroxybenzotriazole hydrate (0.48 g, 3.5 mmol) in acetonitrile (25 mL) at 0° C. The cooling bath was removed and stirring was continued at room temperature for 7 h. The solid was filtered off, washed with acetonitrile and purified by column chromatography on silica using methylene chloride/methanol/triethyl amine, (95:5:0.1), to give 0.68 g (69% yield) of the title compound: 1H NMR (DMSO-d6, 400 MHz) δ 8.53 (m, 1H), 8.34 (s, 1H), 8.68 (br s, 2H), 3.57 (t, J=5 Hz, 4H), 3.37 (q, J=7 Hz, 2H), 2.47 (q, J=7 Hz, 2H), 2.40 (m, 4H); MS (ES) m/z 330 and 332 (M++1).

Provenance & Evidence