2-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochloride → 2-Methyl-1H-imidazole-4-carboxylic acid {2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide hydrochloride
Reaktionsgleichung
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.Cl.[Cl:11][C:12]1[CH:13]=[C:14]([C:19]2[O:23][C:22]([CH2:24][CH2:25][NH2:26])=[CH:21][CH:20]=2)[CH:15]=[CH:16][C:17]=1[Cl:18]>>[ClH:11].[Cl:11][C:12]1[CH:13]=[C:14]([C:19]2[O:23][C:22]([CH2:24][CH2:25][NH:26][C:7]([C:5]3[N:6]=[C:2]([CH3:1])[NH:3][CH:4]=3)=[O:9])=[CH:21][CH:20]=2)[CH:15]=[CH:16][C:17]=1[Cl:18]Komponenten
3
Versuchsvorschrift
The title compound was prepared as in Example 12 starting from 2-methyl-1H-imidazole-4-carboxylic acid and 2-[5-(3,4-dichlorophenyl)furan-2-yl]ethylamine hydrochloride. The crude product was purified by flash chromatography using CH—2Cl2/MeOH as a gradient eluent (100:0-97:3). The product was dissolved in DCM, ethyl acetate saturated with hydrogen chloride was added and the precipitated product as a hydrogen chloride salt was filtered. Recrystallization from MeOH/EtOAc. The HCl salt: 1H NMR (400 MHz, MeOH-d4): 2.62 (3H, s), 3.02 (1H, t), 3.69 (1H, t), 6.26 (1H, d), 6.76 (1H, d), 7.49 (1H, distorted d), 6.53 (1H, distorted dd), 7.71 (1H, d), 7.82 (1H, s).
Aufarbeitung
- customThe crude product was purified by flash chromatography
- dissolutionThe product was dissolved in DCM
- additionethyl acetate saturated with hydrogen chloride was added
- filtrationthe precipitated product as a hydrogen chloride salt was filtered
- customRecrystallization from MeOH/EtOAc
Quellen und Nachweise
- ORD-Eintrag
- ord-1104c7fbe90c4097aa04deb938dc398c
- Quelldatensatz
- uspto-grants-2015_03
- Patentnummer
- US08975254B2
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