Benzeneacetic acid, 4-ethoxy- → HCID 22181344, compound

Participants

Reaction Steps

Following general 13B, (4-ethoxyphenyl)acetic acid (0.0364 g, 0.202 mmol), HATU (0.0768 g, 0.202 mmol), DIPEA (0.048 mL, 0.28 mmol), and 3-amino-N,N-diethyl-4-[(4-pyridinylmethyl)amino]benzamide (0.0548 g, 0.184 mmol) were combined. The crude product was purified by reverse phase MPLC (gradient 10–50% CH3CN in H2O) to provide the title compound (0.0459 g, 36%) as its TFA salt. This material was lyophilized from H2O/dioxane to produce a white solid. 1H-NMR (CD3OD): δ 8.60 (br s, 2H), 7.87 (s, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.52 (dd, J=8.4 Hz, J=2.0 Hz, 1H), 7.42 (d, J=5.6 Hz, 2H), 7.13 (d, J=8.4 Hz, 2H), 6.71 (d, J=9.6 Hz, 2H), 6.06 (s, 2H), 4.54 (s, 2H), 3.93 (q, J=7.2 Hz, 2H), 3.59 (br s, 2H), 3.31 (br s, 2H), 1.35 (t, J=6.8 Hz, 3H), 1.38–1.04 (2×br s, 6H). MS (ESI) (M+H)+443. Anal. Calcd for C27H30N4O2.2.1 TFA. 0.8H2O: C, 53.81; H, 4.88; N, 8.04. Found: C, 53.74; H, 4.89; N, 8.07.

Provenance & Evidence