反应详情

温度

20 °C

0.012 cm3 of 2-fluoro-5-trifluoromethylphenyl isocyanate and 0.012 cm3 of triethylamine are added at a temperature in the region of 20° C., under an argon atmosphere, to 0.017 g (84.48 mmol) of 4-(4-aminophenyl)-1H-pyrrole-3-carboxamide in suspension in 27 cm3 of tetrahydrofuran. After stirring for 20 hours at a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is purified by flash chromatography [eluent: ethyl acetate/dichloromethane (95/5 by volume)]. After concentrating the fractions under reduced pressure, a yellow residue is obtained which is stirred in 5 cm3 of dichloromethane and then filtered and dried under reduced pressure (2.7 kPa) to give 22 mg of 4-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrole-3-carboxamide, in the form of a beige solid; 1H NMR (300 MHz, (CD3)2SO, —δ in ppm): from 6.57 to 7.02 (very broad m: 2H); 6.85 (broad t, J=2.5 Hz: 1H); 7.29 (broad t, J=2.5 Hz: 1H); from 7.33 to 7.43 (m; 5H); 7.49 (dd, J=10.5 and 8.5 Hz: 1H); 8.60 (dd, J=7.5 and 2.5 Hz: 1H); 9.31 (broad s: 1H); 9.58 (broad s: 1H); 11.2 (broad s: 1H); EI: m/z=406 (M+), m/z=205 (C8H3NOF4+), m/z=179 (C7H4NF4+) base peak, ES+: m/z=407 (MH+).

1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
2. customto give a residue which
3. customis purified by flash chromatography [eluent: ethyl acetate/dichloromethane (95/5 by volume)]
4. concentrationAfter concentrating the fractions under reduced pressure
5. customa yellow residue is obtained which
6. filtrationfiltered
7. customdried under reduced pressure (2.7 kPa)