2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 57845549, compound

Participants

Reaction Conditions

Reaction Steps

0.072 cm3 (0.50 mmol) of 2-fluoro-5-trifluoromethylphenyl isocyanate is added at a temperature in the region of 25° C. to 0.170 g (0.50 mmol) of 2-(3-cyclo-pentylpropionylamino)-4-(4-aminophenyl)-1H-pyrrole-3-carboxamide in solution in 20 cm3 of tetrahydrofuran. After stirring for 48 hours at a temperature in the region of 25° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is then diluted in 50 cm3 of ethyl acetate and then washed with 50 cm3 of water and 50 cm3 of a saturated aqueous sodium chloride solution. The organic solution is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is purified by flash chromatography [eluent; dichloromethane/methanol/acetonitrile (95/2.5/2.5 by volume)]. After concentrating the fractions under reduced pressure, 0.048 g of 2-(3-cyclopentylpropionylamino)-4-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrole-3-carboxamide is obtained in the form of a yellow powder melting at 222° C. IR (KBr), 3470; 3389; 1717; 1633; 1594; 1546; 1443; 1341; 1312; 1194; 1167; 1119; 1070 & 614 cm−1. 1H NMR (400 MHz, (CD3)2SO, —δ in ppm) 1.11 (m, 2H); from 1.42 to 1.68 (m, 6H); from 1.71 to 1.85 (m, 3H); 2.40 (t, J=8.0 Hz, 2H); 5.56 (broad m, 1H); 6.39 (d, J=2.5 Hz, 1H); 7.09 (broad m, 1H); 7.30 (d, J=9.0 Hz, 2H); 7.38 (m, 1H); 7.49 (m partially masked, 1H); 7.51 (d, J=9.0 Hz, 2H); 8.62 (dd, J=2.5 and 7.5 Hz, 1H); 9.00 (broad s, 1H); 9.32 (broad s, 1H); 10.8 (broad s, 1H); 11.4 (broad s, 1H).

Provenance & Evidence