Sodium hydride → tert-Butyl{1-[2-(4-oxoquinolin-1(4H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 255331

Reaktionsgleichung

Reaktionsgleichung von HRID 255331
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[H-].[Na+].CS(O[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23][CH2:22]1)(=O)=O.FC1C=C2C(N=CC(=O)N2CCN2CCC(NC(=O)OC(C)(C)C)CC2)=CC=1>>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([NH:27][C:28](=[O:29])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23][CH2:22]2)[CH:2]=[CH:3]1

Komponenten

5

Edukt 4

HCID 24758Sodium hydrideHCID 691414-HydroxyquinolineHCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate2×HCID 59397942tert-butyl{1-[2-(7-fluoro-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Produkt 1

HCID 86642649tert-Butyl{1-[2-(4-oxoquinolin-1(4H)-yl)ethyl]piperidin-4-yl}carbamateAusbeute 76 %

Versuchsvorschrift

Quinolin-4(1H)-one (250 mg, 1.7 mmol) was deprotonated with sodium hydride (60% in oil, 70 mg, 1.7 mmol) and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (1.7 mmol) as described for Intermediate 141. The precipitate formed in the reaction mixture was collected by filtration to give 480 mg (76%) of product as a colorless solid.

Aufarbeitung

  1. customThe precipitate formed in the reaction mixture
  2. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-4ee1e6dc4b9147f48f0b05d74c050d71
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875715B2

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