3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde → 3-[3,5-dimethyl 4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-4-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one

HRID 983105

Reaktionsgleichung

Reaktionsgleichung von HRID 983105
[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.[CH3:19][C:20]1[C:24]([C:25]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)=[O:26])=[C:23]([CH3:34])[NH:22][C:21]=1[CH:35]=O>C(O)C.N1CCCCC1>[CH3:19][C:20]1[C:24]([C:25]([N:27]2[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]2)=[O:26])=[C:23]([CH3:34])[NH:22][C:21]=1[CH:35]=[C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:13][C:12]1=[O:18]

Komponenten

5

Edukt 2

HCID 121115823,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1H-pyrrole-2-carbaldehydeHCID 225618094-(3-Methoxy-phenyl)-1,3-dihydro indol-2-one

Produkt 1

HCID 249426543-[3,5-dimethyl 4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-4-(3-methoxy-phenyl)-1,3-dihydro-indol-2-oneAusbeute 53 %

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 3,5-dimethyl-4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde (64.8 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 3-[3,5-dimethyl 4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-4-(3-methoxy-phenyl)-1,3-dihydro-indol-2-one as a yellow solid (62 mg, 53%)

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-e4490566b70c4db382dd8d38eb7cf348
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861418B2

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