1,2-Dichloro-3-isocyanatobenzene → 1-(5-tert-butyl-2-(5-oxo-1,4-diazepane-1-carbonyl)-1H-pyrrol-3-yl)-3-(2,3-dichloro-phenyl)urea

HRID 18928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18928
[NH2:1][C:2]1[CH:3]=[C:4]([C:17]([CH3:20])([CH3:19])[CH3:18])[NH:5][C:6]=1[C:7]([N:9]1[CH2:15][CH2:14][C:13](=[O:16])[NH:12][CH2:11][CH2:10]1)=[O:8].[Cl:21][C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=1[N:29]=[C:30]=[O:31]>C1COCC1.C(OCC)(=O)C>[C:17]([C:4]1[NH:5][C:6]([C:7]([N:9]2[CH2:15][CH2:14][C:13](=[O:16])[NH:12][CH2:11][CH2:10]2)=[O:8])=[C:2]([NH:1][C:30]([NH:29][C:23]2[CH:24]=[CH:25][CH:26]=[C:27]([Cl:28])[C:22]=2[Cl:21])=[O:31])[CH:3]=1)([CH3:20])([CH3:19])[CH3:18]

Komponenten

5

Edukt 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 586792281-(4-amino-2-tert-butyl-1H-pyrrole-5-carbonyl)-1,4-diazepan-5-one

Produkt 1

HCID 586791281-(5-tert-butyl-2-(5-oxo-1,4-diazepane-1-carbonyl)-1H-pyrrol-3-yl)-3-(2,3-dichloro-phenyl)ureaAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The previously prepared 1-(4-amino-2-tert-butyl-1H-pyrrole-5-carbonyl)-1,4-diazepan-5-one (8 mg, 0.03 mmol) and 2,3 dichlorophenyl isocyanate (5 mg, 0.03 mmol) were dissolved in THF (2 mL) and heated at 70° C. for 2 hours. The reaction mixture was cooled down to room temperature, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, dried and the solvent eliminated under vacuum. The crude product was purified by preparative thin layer chromatography using a mixture of dichloromethane:methanol 9:1 as elution solvent to afford 7.0 mg of 1-(5-tert-butyl-2-(5-oxo-1,4-diazepane-1-carbonyl)-1H-pyrrol-3-yl)-3-(2,3-dichloro-phenyl)urea as a white solid. 1H NMR (400 MHz, acetone-d6): δ (ppm) 9.60 (bs, 1H); 8.60 (d, 2H); 8.26 (d, 1H); 7.30 (t, 1H); 7.20 (d, 1H); 6.84 (t, 1H); 6.59 (d, 1H); 3.76 (m, 2H); 3.70 (m, 2H); 3.40 (m, 2H); 2.61 (m, 2H); 1.37 (s, 9H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. washwashed with saturated aqueous sodium bicarbonate
  3. customdried
  4. customThe crude product was purified by preparative thin layer chromatography
  5. additiona mixture of dichloromethane:methanol 9:1
  6. washas elution solvent

Quellen und Nachweise

ORD-Eintrag
ord-b6ec3c39b59d45f9a0e6cc05adbd1477
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741479B2

Notizen zur Reaktion

Wird geladen…