3-Fluorophenyl isocyanate → Methyl 2-(3-(4-(3-(3-fluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate

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Reaction Steps

To methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate (500 mg) dissolved in THF (10 ml) was added 1-fluoro-3-isocyanatobenzene (260 mg) and stirred at RT overnight. The solid was filtered and washed with THF to yield 460 mg (64%) white solid. MS (ES+): m/z 455 (M+1); 1H NMR (DMSO-d6, 300 MHz): δ 9.19 (d, 1H), 9.16 (s, 1H), 9.13 (s, 1H), 7.84 (d, 2H), 7.67 (s, 1H), 7.62 (d, 2H), 7.5 (dd, 1H), 7.31 (m, 1H), 7.13 (dd, 1H), 6.78 (m, 1H), 4.29 (m, 1H), 3.66 (s, 3H), 2.2 (m, 1H), 0.95 (d, 6H).

Provenance & Evidence