2,6-Lutidine → 1-[5-(6-Chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazol-3-yl]-3-(2-morpholin-4-yl-ethyl)-urea

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)(15 mg, 0.045 mmol), 2,6-lutidine (5.5 mg, 0.052 mmol), 4-nitrophenyl chloroformate (10 mg, 0.05 mmol), and DMA (0.3 mL) was stirred at 25° C. for 10 mins and then 2-morpholin-4-yl-ethylamine (12 mg, 0.092 mmol) was added and stirring continued for 30 mins. The reaction was concentrated and the title compound was purified by RP-HPLC, eluting with 20-50% CH3CN in 0.1% TFA/H2O over 10 mins to give 6 mg (22%) the title cpd as a TFA salt. 1H NMR (400 MHz, CD3OD) δ 7.62 (dd, 1H), 7.52 (m, 3H), 7.44 (m, 2H), 7.30 (m, 2H), 7.12 (d, 1H), 6.60 (s, 1H), 3.72 (m, 4H), 3.40 (m, 2H), 2.52 (m, 6H). Mass spectrum (ESI, m/z) calcd. for C25H24ClN5O4 493.1, found 494.0 (M+H).

Provenance & Evidence