Sodium Hydroxide → Ethyl hydrogen 4-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)phenylphosphonate

Participants

Reaction Conditions

Reaction Steps

A suspension of diethyl [4-({[2-amino-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]phosphonate (24.2 mg, 0.0562 mmol) (24.2 mg, 0.0562 mmol), dioxane (140 uL) and 5N aqueous NaOH (140 uL) was heated to 80° C. (oil bath temperature) for 1 h. The reaction was quenched with TFA (˜140 uL) and concentrated. The residue was purified by HPLC (25-80% MeCN in H2O with 0.025% TFA) to afford the requisite product. 1H NMR (DMSO-d6, 600 MHz) δ 9.77 (s, 1H), 8.30 (t, J=8.3 Hz, 2H), 7.69-7.64 (m, 2H), 7.48-7.45 (m, 1H), 7.34-7.31 (m, 1H), 7.26 (dd, J=8.2, 2.0 Hz, 1H), 7.22 (d, J=2.6 Hz, 1H), 7.02 (dd, J=5.0, 3.5 Hz, 1H), 6.79 (d, J=8.5 Hz, 1H), 5.16 (s, 2H), 3.6-3.54 (m, 2H), 1.05 (t, J=7.04 Hz, 3H). MS: cal'd 403 (MH+), exp 403 (MH+).

Provenance & Evidence