Sodium hydride → Tert-butyl(1-(2-(7-methoxy-2-oxoquinoxalin-1(2h)-yl)ethyl)piperidin-4-yl)carbamate

HRID 1644437

Reaktionsgleichung

Reaktionsgleichung von HRID 1644437
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[H-].[Na+].CS(O[CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][CH2:24]1)(=O)=O.C(OC(=O)NC1CCN(CCN2C3C(=CC=C(OC)C=3)C=CC2=O)CC1)(C)(C)C>CC(C)=O>[C:33]([O:32][C:30](=[O:31])[NH:29][CH:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[N:7]=[CH:8][C:9]2=[O:13])[CH2:24][CH2:25]1)([CH3:36])([CH3:35])[CH3:34]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 4913197-Methoxy-1,2-dihydroquinoxalin-2-one2×HCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate2×HCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Produkt 1

HCID 59398192Tert-butyl(1-(2-(7-methoxy-2-oxoquinoxalin-1(2h)-yl)ethyl)piperidin-4-yl)carbamateAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

7-methoxyquinoxalin-2(1H)-one (Intermediate 148, 300 mg, 1.70 mmol) was deprotonated with sodium hydride (100 mg, 60% in oil, 2.56 mmol) and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (3.4 mmol) as described for Intermediate 2. Chromatography on silica gel with 25% acetone in hexanes gave 200 mg (29%) of the product as a colorless solid.

Quellen und Nachweise

ORD-Eintrag
ord-405e3ba1930e481e9319fb8a234dfce3
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124602B2

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