5-formyl-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diisopropylamino-ethyl)-amide → 5-[4-(3-methoxy-phenyl) 2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diisopropylamino-ethyl)-amide

HRID 1839722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1839722
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][C:12](=[O:18])[NH:13]3)[CH:6]=[CH:7][CH:8]=1.[CH:19]([N:22]([CH:37]([CH3:39])[CH3:38])[CH2:23][CH2:24][NH:25][C:26]([C:28]1[C:32]([CH3:33])=[C:31]([CH:34]=O)[NH:30][C:29]=1[CH3:36])=[O:27])([CH3:21])[CH3:20]>C(O)C.N1CCCCC1>[CH:37]([N:22]([CH:19]([CH3:21])[CH3:20])[CH2:23][CH2:24][NH:25][C:26]([C:28]1[C:32]([CH3:33])=[C:31]([CH:34]=[C:11]2[C:10]3[C:14](=[CH:15][CH:16]=[CH:17][C:9]=3[C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:13][C:12]2=[O:18])[NH:30][C:29]=1[CH3:36])=[O:27])([CH3:38])[CH3:39]

Komponenten

5

Edukt 2

HCID 207617895-formyl-2,4-dimethyl-1 H-pyrrole-3-carboxylic acid (2-diisopropylamino-ethyl)-amideHCID 225618094-(3-Methoxy-phenyl)-1,3-dihydro indol-2-one

Produkt 1

HCID 249413505-[4-(3-methoxy-phenyl) 2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diisopropylamino-ethyl)-amideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one (59.8 mg, 0.25 mmol) and 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diisopropylamino-ethyl)-amide (73 mg, 0.25 mmol) in ethanol (2 mL) was added piperidine (3 drops). The reaction mixture was stirred at room temperature for three days. The reaction solution was evaporated, and purified on a silica gel column eluting with MeOH—CH2Cl2 5:95 to provide pure product 5-[4-(3-methoxy-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diisopropylamino-ethyl)-amide as a yellow solid (95 mg, 79%).

Aufarbeitung

  1. customThe reaction solution was evaporated
  2. custompurified on a silica gel column
  3. washeluting with MeOH—CH2Cl2 5:95

Quellen und Nachweise

ORD-Eintrag
ord-b952fe865a9c4b86babed120ae161f17
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677368B2

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