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 2116788Notes

Reaction equation

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

Participants

Conditions

Temperature: 68 °C

Procedure

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).

Workup

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)

Sources & evidence

ORD record: ord-7602790689d64d8886429c7ffe176062
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439371B2

Reaction notes

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