Morpholine → HCID 178521260, compound

Participants

Reaction Steps

6-Bromo-1-(2-morpholino-2-oxoethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one-2,2,2-trifluoroacetate. 2-(6-Bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyrazin-1-yl)acetic acid (141 mg, 0.516 mmol) and 1,1′-carbonyldiimidazole (256 mg, 1.58 mmol) were combined in a round-bottom flask with a stirbar. Methylene chloride (6 mL) was added and the resulting mixture stirred at room temperature under nitrogen. DMF (2 mL) was added. All of the solids dissolved. The resulting clear reaction mixture was stirred at room temperature under nitrogen for 2.5 h at which time morpholine (0.34 mL, 3.90 mmol) was added. The resulting mixture was stirred at room temperature for 1 h. The methylene chloride was removed on a rotary evaporator. The resulting mixture was diluted with methanol, filtered, and purified using reverse-phase preparatory HPLC (5-50% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). Vials containing product were combined and all of the solvent removed on a rotary evaporator. The residue was dried under vacuum to give the desired product (209 mg, 89%) as a slightly yellow foam-solid. 1H NMR (400 MHz, DMSO-d6) δ 12.36 (s, 1H), 8.09 (s, 1H), 4.78 (s, 2H), 3.63-3.69 (m, 2H), 3.55-3.62 (m, 4H), 3.43 (t, J=4.88, 2H); MS (ESI) m/z 342[M+1]+.

Provenance & Evidence