Hydrochloric Acid → HCID 67213118, compound

Participants

Reaction Conditions

Reaction Steps

To 0.15 g (0.288 mmol) of 4-tert-butyloxycarbonylamino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrole-2-carboxamide suspended in 1 cm3 of dioxane is added, at a temperature in the region of 20° C., 0.72 cm3 of a 4N solution of hydrogen chloride in dioxane. After stirring for 5 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: dichloromethane/methanol/acetonitrile (gradient of from 90/5/5 to 80/10/10 by volume)]. After concentrating the fractions under reduced pressure, 85 mg of a yellow solid are obtained, and are then stirred in 4 cm3 of pentane for 16 hours. After filtering through a No 3 sinter funnel, the solid is washed with twice 1 cm3 of pentane and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. for 4 hours to give 47 mg of 4-amino-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrole-2-carboxamide hydrochloride in the form of a yellow solid melting at about 174° C.; 1H NMR (400 MHz, DMSO d6, δ in ppm) from 5.30 to 8.00 (very broad m, 2H); 6.34 (d, J=2.5 Hz, 1H); 7.27 (d, J=8.5 Hz, 2H); 7.39 (m, 1H); 7.50 (partially masked m, 1H); 7.53 (d, J=8.5 Hz, 2H); 8.63 (broad d, J=7.0 Hz, 1H); 8.96 (broad s, 1H); 9.29 (s, 1H); 10.7 (broad s, 1H):; ES+: m/z=422: [M+H]+; ES−: m/z=420: [M−H]−.

Provenance & Evidence