Diisopropylethylamine → (S)-N-ethyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide
Reaktionsgleichung
O[CH2:2][C:3]1[CH:12]=[N:11][C:10]2[N:9]3[CH2:13][CH2:14][CH2:15][C@H:8]3[C:7](=[O:16])[NH:6][C:5]=2[CH:4]=1.[I-].C(C[P+](C)(C)C)#N.[CH2:25]([NH:27][C:28](=[O:41])[C:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[CH:31][CH:30]=1)[CH3:26].CCN(C(C)C)C(C)C>C(#N)CC.CS(C)=O>[CH2:25]([NH:27][C:28](=[O:41])[C:29]1[CH:30]=[CH:31][C:32]([N:35]2[CH2:36][CH2:37][N:38]([CH2:2][C:3]3[CH:12]=[N:11][C:10]4[N:9]5[CH2:13][CH2:14][CH2:15][C@H:8]5[C:7](=[O:16])[NH:6][C:5]=4[CH:4]=3)[CH2:39][CH2:40]2)=[CH:33][CH:34]=1)[CH3:26]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a suspension of (S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (0.8 g, 3.65 mmol)) in propiononitrile (Volume: 27.4 ml) was added (cyanomethyl)trimethylphosphonium iodide (1.064 g, 4.38 mmol), N-ethyl-4-(piperazin-1-yl)benzamide (0.851 g, 3.65 mmol) and DIEA (1.912 ml, 10.95 mmol). The vial was heated to 90° C. for 16 hours. The crude reaction was cooled to RT, DMSO (1 ml) was added, and the mixture was purified via HPLC (55-90, basic) to give the product as a white solid.
Aufarbeitung
- customThe crude reaction
- temperaturewas cooled to RT
- customthe mixture was purified via HPLC (55-90, basic)
Quellen und Nachweise
- ORD-Eintrag
- ord-9fc43a7fa9e6457ca5488b23c8f0c36f
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08822470B2
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