Triethylamine → 4-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrole-3-carboxamide

HRID 734626Notes

Reaction equation

HRID 734626 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N:12]=[C:13]=[O:14].C(N(CC)CC)C.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[C:30]([C:34]([NH2:36])=[O:35])=[CH:31][NH:32][CH:33]=2)=[CH:25][CH:24]=1>O1CCCC1.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13](=[O:14])[NH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[C:30]([C:34]([NH2:36])=[O:35])=[CH:31][NH:32][CH:33]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 451167614-(4-aminophenyl)-1H-pyrrole-3-carboxamide

Product 1

HCID 115750214-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-aedb505d8e6f41e4a9b6ab3e3802a768
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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