Reaktionsgleichung
CO[CH:3](OC)[CH:4]([NH2:6])[CH3:5].[C:9](N1C=CN=C1)(N1C=CN=C1)=[S:10].C(N(CC)CC)C.[N:28]1([CH2:33][CH2:34][CH2:35][O:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3([CH2:49][NH2:50])[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)=[CH:39][CH:38]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1.Cl>CN(C=O)C>[CH3:3][C:4]1[N:6]=[C:9]([SH:10])[N:50]([CH2:49][C:43]2([C:40]3[CH:41]=[CH:42][C:37]([O:36][CH2:35][CH2:34][CH2:33][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:38][CH:39]=3)[CH2:44][CH2:45][O:46][CH2:47][CH2:48]2)[CH:5]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
2-Aminopropionaldehyde dimethyl acetal (0.2 g, 1.7 mmol), thiocarbonyldiimidazole (0.36 g, 2.0 mmol) and triethylamine (0.23 ml, 1.7 mmol) were stirred in DMF (2.0 ml) at ambient temperature for 30 minutes before heating to 50° C. for 18 hours. {4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (540 mg, 1.7 mmol) was added and stirred at ambient temperature for 4 hours. 2M HCl (6 ml) was added, stirred at 70° C. for 18 hours, then c.HCl (1.0 ml) was added and the mixture stirred at 110° C. for 18 hours. The reaction mixture was cooled and partitioned between ethyl acetate (100 ml) and dilute aqueous sodium carbonate (50 ml). The organics were dried over Na2SO4 and concentrated in vacuo to give the title compound as a grey solid (600 mg, 84%). LRMS ESI+ m/z 416 [M+H]+.
Aufarbeitung
- stirringstirred at 70° C. for 18 hours
- stirringthe mixture stirred at 110° C. for 18 hours
- temperatureThe reaction mixture was cooled
- custompartitioned between ethyl acetate (100 ml) and dilute aqueous sodium carbonate (50 ml)
- dry with materialThe organics were dried over Na2SO4
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-b796efc69428456c880e5d7cce14c0cf
- Quelldatensatz
- uspto-grants-2008_11
- Patentnummer
- US07456164B2
Verknüpfte Notizen
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