Diethylamine → N,N-Diethyl-6-methoxy-9-oxo-9H-xanthene-3-carboxamide

Participants

Reaction Steps

A mixture of compound 6i (0.707 g, 2.62 mmol) and O-benzotriazol-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU, 1.05 g, 2.74 mmol) in N,N-dimethylformamide (10 mL) was treated with N,N-diisopropylethylamine (DIEA, 0.685 mL, 3.92 mmol) and allowed to stir at rt for 15 min. Diethylamine (0.541 mL, 5.23 mL) was added and the resultant mixture was stirred for 2 h. The mixture was poured into ice water. A solid was collected by filtration, washed with water and air dried to give the title compound (0.445 g). MS: m/z 326.0 (MH+). 1H NMR (DMSO-d6): δ 1.07 (br t, 3H), 1.19 (br t, 3H), 3.20 (br q, 2H), 3.48 (br t, 2H), 3.95 (s, 3H), 7.08 (m, 1H), 7.17 (d, 1H, J=2.1 Hz), 7.40 (d of d, 1H, J=1.3 & 8.1 Hz), 7.59 (d, 1H, J=1.2 Hz), 8.12 (d of d, 1H, J=1.3 & 8.9 Hz) and 8.21 (d, 1H, J=8.1 Hz).

Provenance & Evidence