2,6-Lutidine → N'-[5-(6-Chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazol-3-yl]-N,N-dimethyl-formamidine

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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), methanesulfonyl chloride (7.4 mg, 0.065 mmol), 2,6-lutidine (7.4 mg, 0.068 mmol), and DMF (0.1 mL) was stirred at 25° C. for 2 hrs. The reaction was concentrated and the title compound was purified by RP-HPLC, eluting with 40-70% CH3CN in 0.1% TFA/H2O over 20 mins to give 15 mg (68%) the title cpd as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ 12.62 (s, 1H), 8.52 (s, 1H), 7.68 (dd, 1H), 7.48 (m, 4H), 7.32 (m, 2H), 6.96 (d, 1H), 6.80 (s, 1H), 3.25 (s, 3H), 3.12 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C21H17ClN4O2 392.1, found 393.1 (M+H).

Provenance & Evidence