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 2116791Notes

Reaction equation

CN1C(NC(=O)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][C:16]2[CH:24]=[C:23]3[C:19](/[C:20](=[CH:26]/O)/[C:21](=[O:25])[NH:22]3)=[CH:18][CH:17]=2)=CC(C)=N1.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=2)[CH2:33][CH2:32]1>C1COCC1>[CH3:23][NH:22][C:21](=[O:25])[C:12]1[CH:13]=[CH:14][CH:9]=[C:10]([S:15][C:16]2[CH:24]=[C:23]3[C:19]([C:20](=[CH:26][NH:43][C:40]4[CH:41]=[CH:42][C:37]([N:34]5[CH2:33][CH2:32][N:31]([CH3:30])[CH2:36][CH2:35]5)=[CH:38][CH:39]=4)[C:21](=[O:25])[NH:22]3)=[CH:18][CH:17]=2)[CH:11]=1

Participants

Conditions

Temperature: 68 °C

Procedure

A 1 mL vial was charged with N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-{3-[1-hydroxy-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl}-benzamide (as prepared below; 55 mg, 0.135 mmol), 4-(4-methyl-piperazin-1-yl)-phenylamine (25.8 mg, 0.138 mmol), and THF (1 mL). This reaction mixture was stirred for 24 h at 68° C. Subsequently, the reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was re-suspended in EtOAc (5 mL) and extracted with H2O (˜5 mL). The organic layer was concentrated in vacuo and the residue was chromatographed via flash silica gel chromatography (gradient of 1-10% MeOH in CHCl3) afforded the title compound in 35% yield (27 mg, 0.047 mmol).

Workup

temperatureSubsequently, the reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
extractionextracted with H2O (˜5 mL)
concentrationThe organic layer was concentrated in vacuo
customthe residue was chromatographed via flash silica gel chromatography (gradient of 1-10% MeOH in CHCl3)

Sources & evidence

ORD record: ord-4292fd30e80648e9b9a42c0f1966af1a
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439371B2

Reaction notes

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