1-(3-Isocyanatophenyl)ethan-1-one → 1-(3-Acetyl-phenyl)3-[3-(4-fluoro-2-methyl-2H-pyrazol-3-yl)4-methoxy-phenyl]-urea

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Reaction Steps

3-(4-Fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine was treated with 3-acetylphenylisocyanate, in a similar manner as described in Example 1.68. An additional purification by flash chromatography (SiO2, Hexanes/EtOAc gradient elution) was necessary, providing 36 mg (53% yield) of Compound 88: LCMS m/z (%)=383 (M+H, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.31 (s, 1H), 8.17 (s, 1H), 8.13 (s, 1H), 7.79 (dd, J1=9.0 Hz, J2=2.2 Hz, 1H), 7.63 (d, J1=15.5 Hz, J2=8.3 Hz, J3=2.7 Hz, 1H), 7.50 (d, J=2.4 Hz, 1H), 7.41 (m, 3H), 7.14 (d, J=9.2 Hz, 1H), 3.84 (s, 3H), 3.65 (s, 3H), 2.56 (s, 3H). 19F NMR (376 MHz, acetone-d6) δ: −177.39 (d, JH,F=4.1 Hz, 1F).

Provenance & Evidence