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

HRID 1644459

Reaction equation

HRID 1644459 reaction equation
[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.C(OC(=O)NC1CCN(CCN2C3C(=CC=C(F)C=3)N=CC2=O)CC1)(C)(C)C>>[C:31]([O:30][C:28](=[O:29])[NH:27][CH:24]1[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[CH:3]=[CH:2]2)[CH2:22][CH2:23]1)([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 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

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-df4c9b3a16b84dcdb2697ae9c808c21c
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Linked notes

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