Acetic Anhydride → N-[5-(6-Chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazol-3-yl]-acetamide

Participants

Reaction Conditions

Reaction Steps

A flask charged with 3-(3-amino-isoxazol-5-yl)-6-chloro-4-phenyl-1H-quinolin-2-one (example 59)(22 mg, 0.063 mmol), acetic anhydride (9 mg, 0.082 mmol), 2,6-lutidine (11 mg, 0.10 mmol), DMAP (10 mg, 0.082 mmol) and DMF (0.5 mL) was heated at 50° C. for 2 hrs. The reaction was concentrated and the title compound was purified by RP-HPLC, eluting with 40-100% CH3CN in 0.1% TFA/H2O over 30 mins to give 15 mg (60%) the title cpd. 1H NMR (400 MHz, DMSO-d6) δ 12.54 (s, 1H), 10.80 (s, 1H), 7.68 (m, 1H), 7.46 (m, 4H), 7.30 (m, 2H), 6.96 (m, 2H), 2.04 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C20H14ClN3O3 379.1, found 380.0 (M+H).

Provenance & Evidence