4-(4-Methylpiperazin-1-yl)aniline → N-methyl-3-[[3-[[4-(4-methylpiperazin-1-yl)anilino]methylidene]-2-oxo-1H-indol-6-yl]sulfanyl]benzamide

HRID 2116788Notizen

Reaktionsgleichung

O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12][C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=3)[C:16]([NH:18][CH3:19])=[O:17])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:23].[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1>C1COCC1>[CH3:19][NH:18][C:16](=[O:17])[C:15]1[CH:20]=[CH:21][CH:22]=[C:13]([S:12][C:8]2[CH:7]=[C:6]3[C:11]([C:3](=[CH:2][NH:37][C:34]4[CH:33]=[CH:32][C:31]([N:28]5[CH2:27][CH2:26][N:25]([CH3:24])[CH2:30][CH2:29]5)=[CH:36][CH:35]=4)[C:4](=[O:23])[NH:5]3)=[CH:10][CH:9]=2)[CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 68 °C

Versuchsvorschrift

A small screw cap test tube was charged with 3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-N-methyl-benzamide (as prepared below; 20 mg, 0.062 mmol) and THF (1 mL). To the resulting solution was added 4-(4-methyl-piperazin-1-yl)-phenylamine (12 mg, 0.062 mmol), and the mixture was stirred for 24 h at 68° C. Subsequently, the reaction mixture was cooled to room temperature and then concentrated in vacuo. Purification of the crude residue via flash silica gel chromatography (10% MeOH in CHCl3) afforded the title compound in 39% yield (12 mg, 0.024 mmol).

Aufarbeitung

customA small screw cap test tube
temperatureSubsequently, the reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
customPurification of the crude residue via flash silica gel chromatography (10% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag: ord-7602790689d64d8886429c7ffe176062
Quelldatensatz: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07439371B2

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