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

HRID 227680Notes

Reaction equation

HRID 227680 reaction equation
[Cl:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[C:4]([C:7]([NH2:9])=[O:8])[NH:5][CH:6]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=1[N:28]=[C:29]=[O:30]>O1CCCC1>[Cl:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:29]([NH:28][C:19]3[CH:20]=[C:21]([C:24]([F:25])([F:27])[F:26])[CH:22]=[CH:23][C:18]=3[F:17])=[O:30])=[CH:12][CH:11]=2)=[C:4]([C:7]([NH2:9])=[O:8])[NH:5][CH:6]=1

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 67212936HCID 67212936, compound

Product 1

HCID 577568844-chloro-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrole-2-carboxamideYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To 0.03 g (0.127 mmol) of 4-chloro-3-(4-aminophenyl)-1H-pyrrole-2-carboxamide dissolved in 2.7 cm3 of tetrahydrofuran is added, at a temperature in the region of 20° C. under an argon atmosphere, 0.019 cm3 (0.134 mmol) of 2-fluoro-5-trifluoromethylphenyl isocyanate. After stirring for 2 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 recrystallized from 4 cm3 of acetonitrile. After filtering through a No. 3 sinter funnel, the solid is washed with 2 cm3 of acetonitrile and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 45° C. for 2 hours to give 0.037 g of 4-chloro-3-{4-[3-(2-fluoro-5-trifluoromethylphenyl)-ureido]phenyl}-1H-pyrrole-2-carboxamide in the form of a white solid; 1H NMR (400 MHz, DMSO d6, δ in ppm): 5.83 (broad m, 1H); 7.08 (s, 1H); 7.18 (broad m, 1H); 7.28 (d, J=8.5 Hz, 2H); 7.38 (m, 1H); 7.50 (partially masked m, 1H); 7.55 (d, J=8.5 Hz, 2H); 8.62 (dd, J=2.0 and 7.5 Hz, 1H); 9.04 (broad s, 1H); 9.39 (broad s, 1H); 11.8 (broad s, 1H); ES+: m/z=441: [M+H]+; ES−: m/z=439: [M−H]−.

Workup

  1. additionis added, at a temperature in the region of 20° C. under an argon atmosphere
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue, which
  4. customis recrystallized from 4 cm3 of acetonitrile
  5. filtrationAfter filtering through a No
  6. wash3 sinter funnel, the solid is washed with 2 cm3 of acetonitrile
  7. customdried under reduced pressure (2.7 kPa) at a temperature in the region of 45° C. for 2 hours

Sources & evidence

ORD record
ord-a6d188cb463d4b62a0140aeefe00afe0
Source dataset
uspto-grants-2009_07
Patent number
US07560571B2

Reaction notes

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