1,1'-Carbonyldiimidazole → 3-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-one

HRID 1008111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1008111
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:18])[NH:11][C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[CH:19]1[N:23]=[CH:22][N:21]([C:24](N2C=NC=C2)=[O:25])[CH:20]=1>CN(C=O)C>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:18])[N:11]([C:24]([N:21]2[CH:20]=[CH:19][N:23]=[CH:22]2)=[O:25])[C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 5329098Semaxanib

Produkt 1

HCID 601112313-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-oneAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A reaction mixture of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole (1.0 gram, 4.2 mmol) and CDI (1.36 gram 8.4 mmol) in DMF was stirred at room temperature for 2 h and filtered. The precipitate was washed with DMF and dried in a high vacuum oven to give 1.25 gram (89%) of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-one as an orange solid. 1HNMR (400 MHz, DMSO-d6) δ 12.23 (s, 1H, NH-1′), 8.45 (s, 1H), 7.94 (m, 1H), 7.79 (m, 1H), 7.73 (s, 1H, H-vinyl), 7.46 (m, 1H), 7.25 (m, 2H), 7.13 (m, 1H), 6.14 (d, J=1.95 Hz, 1H, H-4′), 2.36 (s, 3H, CH3), and 2.32 (s, 3H, CH3). MS m/z (relative intensity, %) 332 (100, M+.)

Aufarbeitung

  1. filtrationfiltered
  2. washThe precipitate was washed with DMF
  3. customdried in a high vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-cbfd953bf06d438fa159e43215d448e0
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797725B2

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