Water → HCID 178461553, Verbindung
Reaktionsgleichung
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7](C3C=CC=C4C=3C=CN4)[NH:8]2)=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][C@H:21]2C)[N:3]=1.[O:27]1[CH2:33][CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[CH3:34]CN(C(C)C)C(C)C.O>C(O)CCC>[CH3:34][C@@H:28]1[O:27][C@H:33]([CH3:32])[CH2:31][N:30]([C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][NH:8]3)=[C:4]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[N:3]=2)[CH2:29]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
To the solution of 2-chloro-8-(1H-indol-4-yl)-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (50 mg, 0.14 mmol) in 1-butanol (300 μL) was added 1,4-oxazepane (20.6 mg, 0.20 mmol), followed by DIPEA (47.4 μL, 0.27 mmol). The mixture was stirred at 120° C. for 24 hours. Upon completion of the reaction, the solution was poured into water. The aqueous layer was extracted with CH2Cl2 three times. The combined organic layers were dried over Na2SO4, filtered, concentrated under reduced pressure and the crude was purified by flash column chromatography (30-100% EtOAc/cyclohexane gradient) to provide 2-((2S,6R)-2,6-dimethyl-morpholin-4-yl)-6-morpholin-4-yl-9H-purine (35 mg, 59%) as a beige solid. LC-MS at 254 nm; [M+H] 432.3; Rt 1.00 min; (LCMS method 1).
Aufarbeitung
- customUpon completion of the reaction
- extractionThe aqueous layer was extracted with CH2Cl2 three times
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customthe crude was purified by flash column chromatography (30-100% EtOAc/cyclohexane gradient)
Quellen und Nachweise
- ORD-Eintrag
- ord-37f2b30fc4ee4019a1389f24dd1dcbfa
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09334271B2
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