Sodium hydride → tert-Butyl{1-[2-(6,7-dimethoxy-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 1644450Notes

Reaction equation

HRID 1644450 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8](=[O:15])[CH:7]=[N:6]2.[H-].[Na+].CS(O[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:27][CH2:26]1)(=O)=O.C(OC(=O)NC1CCN(CCN2C3C(=CC=C(OC)C=3)C=CC2=O)CC1)(C)(C)C>CC(C)=O>[C:35]([O:34][C:32](=[O:33])[NH:31][CH:28]1[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][N:9]2[C:10]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=3)[N:6]=[CH:7][C:8]2=[O:15])[CH2:26][CH2:27]1)([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 113332106,7-Dimethoxyquinoxalin-2-ol2×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

Product 1

HCID 86642646tert-Butyl{1-[2-(6,7-dimethoxy-2-oxoquinoxalin-1(2H)-yl)ethyl]piperidin-4-yl}carbamateYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6,7-Dimethoxyquinoxalin-2(1H)-one (Intermediate 158, 540 mg, 2.60 mmol) was deprotonated with sodium hydride (60% in oil, 2.90 mmol) and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (3.9 mmol) as described for Intermediate 2. Chromatography on silica gel with 20-50% acetone in hexanes gave 310 mg (28%) of the product as an off-white solid.

Sources & evidence

ORD record
ord-cd57c768abdd4241ae4f6ab4f80961d3
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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