2-Methoxyethylamine → HCID 68544478, compound

Participants

Reaction Steps

2-Oxoindoline-5-carboxylic acid (0.470 g, 2.66 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (1.010 g, 3.15 mmol), 1-hydroxybenzotriazole hydrate (0.417 g, 3.09 mmol) and N,N-diisopropylethylamine (0.7 mL, 4.0 mmol) were suspended in acetonitrile/N,N-dimethylformamide, (10 mL:2 mL), and stirred at room temperature for 30 min. 2-Methoxyethanamine (0.516 g, 6.88 mmol) was added and stirring was continued for 2 h. Saturated aqueous sodium hydrogencarbonate was added (10 mL) and the solvents were removed in vacuo. The residue was purified on a silica gel column using a gradient chloroform/methanol, (100:1 to 1:1), as the eluent to give 0.355 g (57% yield) of the title compound as a solid: 1H NMR (DMSO-d6, 400 MHz) δ 10.59 (s, 1H), 8.31 (m, 1H), 7.72 (d, J=7 Hz, 1H), 7.71 (s, 1H), 6.83 (d, J=8 Hz, 1H), 3.51 (s, 2H), 3.42 (m, 2H), 3.39 (m, 2H), 3.24 (s, 3H); MS (ES) m/z 235 (M++1).

Provenance & Evidence