3,5-Dimethylisoxazole-4-isocyanate → HCID 25255370, Verbindung

HRID 507403

Reaktionsgleichung

Reaktionsgleichung von HRID 507403
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]2[CH3:25])=[CH:4][CH:3]=1.[N:27]([C:30]1[C:31]([CH3:36])=[N:32][O:33][C:34]=1[CH3:35])=[C:28]=[O:29]>ClCCl>[CH3:36][C:31]1[C:30]([NH:27][C:28]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:26])[CH2:9][N:10]3[C:14](=[O:15])[C:13]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]3[CH3:25])=[CH:6][CH:7]=2)=[O:29])=[C:34]([CH3:35])[O:33][N:32]=1

Komponenten

4

Edukt 2

HCID 27362663,5-Dimethylisoxazole-4-isocyanateHCID 68467135HCID 68467135, Verbindung

Produkt 1

HCID 25255370HCID 25255370, VerbindungAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (+/−)-3-[2-(4-amino-phenyl)-2-oxo-ethyl]-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one (88 mg, 0.25 mmol) and 4-isocyanato-3,5-dimethyl-isoxazole (35 mg, 0.25 mmol) in 3 mL dichloromethane is stirred at room temperature for 18 hours. Subsequently the solvent is evaporated and the residue is dissolved in acetonitrile, the solution filtrated and subjected to preparative HPLC purification (method 3) to yield (+/−)-1-(3,5-dimethyl-isoxazol-4-yl)-3-{4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-urea (43 mg, 35%), LC/MS at 254 nm; [M+H] 488; Rt 2.648 min.

Aufarbeitung

  1. customSubsequently the solvent is evaporated
  2. dissolutionthe residue is dissolved in acetonitrile
  3. filtrationthe solution filtrated
  4. customsubjected to preparative HPLC purification (method 3)

Quellen und Nachweise

ORD-Eintrag
ord-788ec14dbf054e259be1b6dbb050e94f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786155B2

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