3-(4-Aminophenyl)propionic acid → HCID 178428789, Verbindung

HRID 641037

Reaktionsgleichung

O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[O:24][CH:25]=[CH:26][C:27]=4[CH3:28])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:29].[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:33][CH:32]=1>C1COCC1>[CH3:28][C:27]1[CH:26]=[CH:25][O:24][C:23]=1[C:21]([NH:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:3](=[CH:2][NH:30][C:31]3[CH:32]=[CH:33][C:34]([CH2:37][CH2:38][C:39]([OH:41])=[O:40])=[CH:35][CH:36]=3)[C:4](=[O:29])[NH:5]2)=[CH:10][CH:9]=1)=[O:13])=[O:22]

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

A small screw cap test tube was charged with 3-Methyl-furan-2-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 354, 200 mg, 0.515 mmol) and THF (5.0 mL). To the resulting solution was added 3-(4-Amino-phenyl)-propionic acid (85.1 mg, 0.515 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was purified by flash silica gel chromatography (EtOAc:MeOH mix eluant with gradient of 1% MeOH to 10% MeOH) to afford the title compound in 57% yield (0.157 g, 0.293 mmol).

Aufarbeitung

customA small screw cap test tube
temperatureSubsequently, the reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
customThe crude residue was purified by flash silica gel chromatography (EtOAc:MeOH mix eluant with gradient of 1% MeOH to 10% MeOH)

Quellen und Nachweise

ORD-Eintrag: ord-74496137741a489dbb87253cb917ed3b
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07692005B2

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