Ethanol → HCID 25205624, Verbindung
Reaktionsgleichung
[C:1]([C:3](=[CH:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:4]([NH2:6])=[S:5])#[N:2].N1(O)[CH2:17][CH2:16][CH2:15]C1.[NH:19]1[CH2:24][CH2:23]O[CH2:21][CH2:20]1.Cl[CH2:26][C:27]([NH2:29])=[O:28].[C:30]([O-:33])([O-])=[O:31].[K+].[K+].[CH2:36](O)C>>[C:16]([O:33][C:30]([N:19]1[CH2:20][C:21]2[N:6]=[C:4]3[C:3]([C:1]([NH2:2])=[C:26]([C:27](=[O:28])[NH2:29])[S:5]3)=[C:7]([C:8]3[S:9][CH:10]=[CH:11][CH:12]=3)[C:23]=2[CH2:24]1)=[O:31])([CH3:15])([CH3:17])[CH3:36]Komponenten
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a mixture of 2-cyano-3-thiophen-2-yl-thioacrylamide (4.38 g, 22.5 mmol) and 1-boc-3-pyrrolidine synthesized from pyrrolidinol by reference procedures (Synthetic Commun. 1985, 15(7), 587-598) (4.16 g, 22.5 mmol) in 200 ml of anhydrous ethanol was added morpholine (3.94 g, 45 mmol) at room temperature with stirring. The resulting mixture was heated to reflux overnight. Then, 2-chloroacetamide (4.21 g, 45 mmol) and K2CO3 (6.23 g, 45 mmol) were added. The reaction mixture was continued to heat at 80° C. overnight and then cooled to room temperature. The crystals was filtered and washed with ethanol and water to give the desired product as yellow crystals. 1H-NMR (300 MHz, DMSO-d6): δ 7.92 (dd, J=1.2, 5.1 Hz, 1H), 7.33 (dd, J=1.2, 3.6 Hz, 1H), 7.30 (dd, J=3.6, 5.1 Hz, 1H), 7.26 (brs, 1H), 5.97 (d, J=10.5 Hz, 2H), 4.70 (d, J=6.0 Hz, 2H), 4.45 (d, J=10.5 Hz, 2H), 1.42 (m, 9H). ES MS m/z 417 (M+H)+, 415 (M−H)−.
Aufarbeitung
- temperatureThe resulting mixture was heated
- temperatureto reflux overnight
- temperaturecooled to room temperature
- filtrationThe crystals was filtered
- washwashed with ethanol and water
Quellen und Nachweise
- ORD-Eintrag
- ord-fe7138dc431a4a759e6578fc2e63023a
- Quelldatensatz
- uspto-grants-2008_12
- Patentnummer
- US07465742B2
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