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

HRID 734650

Reaktionsgleichung

Reaktionsgleichung von HRID 734650
[F:1][C:2]1[CH:3]=[C:4]([N:12]=[C:13]=[O:14])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:15]([NH:18][C:19]1[NH:20][CH:21]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=2)[C:23]=1[C:24]([NH2:26])=[O:25])(=[O:17])[CH3:16]>O1CCCC1>[C:15]([NH:18][C:19]1[NH:20][CH:21]=[C:22]([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:13]([NH:12][C:4]3[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=[C:2]([F:1])[CH:3]=3)=[O:14])=[CH:29][CH:28]=2)[C:23]=1[C:24]([NH2:26])=[O:25])(=[O:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 34456721-Fluoro-3-isocyanato-5-(trifluoromethyl)benzeneHCID 690618602-acetylamino-4-(4-aminophenyl)-1H-pyrrole-3-carboxamide

Produkt 1

HCID 578455512-acetylamino-4-{4-[3-(3-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrole-3-carboxamideAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.061 cm3 (0.426 mmol) of 3-fluoro-5-trifluoromethylphenyl isocyanate is added at room temperature to a suspension of 100 mg (0.387 mmol) of 2-acetylamino-4-(4-aminophenyl)-1H-pyrrole-3-carboxamide in 5 cm3 of anhydrous tetrahydrofuran. The reaction medium is stirred at room temperature for 24 hours, cooled in a water-ice bath and then filtered on sintered glass. The solid collected is washed with a small amount of dichloromethane and cyclohexane and then dried under vacuum. 75 mg of 2-acetylamino-4-{4-[3-(3-fluoro-5-trifluoromethylphenyl)ureido]phenyl}-1H-pyrrole-3-carboxamide are obtained in the form of a beige solid.

Aufarbeitung

  1. temperaturecooled in a water-ice bath
  2. filtrationfiltered on sintered glass
  3. customThe solid collected
  4. washis washed with a small amount of dichloromethane and cyclohexane
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4cd57cb910dd432b8625224f499fdc1c
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592365B2

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