Phenyl isocyanate → 1-[4-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)cyclopent-2-enyl]3-phenyl-urea

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Reaction Steps

To a stirred solution of 5-(4amino-cyclopent-2-enyl)9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (50 mg, 0.16 mmol) in CH2Cl2 (2 mL) was added isocyanatobenzene (0.018 mL, 0.18 mmol) and DMAP (catalytic amount) and stirred at r.t for 2 hours. The mixture was diluted with CH2Cl2, washed (brine), dried (Na2SO4), filtered and concentrated Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave the tide compound (35 mg, 50%). Mass Spectrum (M) (m/z) 433.3 (M−1). Anal. Calc. For C23H19ClN4O3; Theoretical: C, 63.52, H, 4.40, N, 12.88%; Found: C, 63.82, H, 4.45, N, 12.49%.

Provenance & Evidence