Sodium hydride → HCID 86642628, compound

HRID 1644378Notes

Reaction equation

HRID 1644378 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3](=[O:11])[CH2:2]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(OC)C=3)C=CC2=O)CC1)(C)(C)C>ClCCl.CO>[C:31]([O:30][C:28](=[O:29])[NH:27][CH:24]1[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][N:4]2[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[O:1][CH2:2][C:3]2=[O:11])[CH2:22][CH2:23]1)([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 727572H-1,4-benzoxazin-3(4H)-oneHCID 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 86642628HCID 86642628, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

2H-1,4-Benzoxazin-3(4H)-one (298 mg, 2.0 mmol) was deprotonated with sodium hydride and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (2.0 mmol) as described for Intermediate 2. Chromatography on silica gel with dichloromethane/methanol (20:1) gave the product in 63% yield as a yellow gum.

Sources & evidence

ORD record
ord-25d372272d6c458d8fd164e6fe150e33
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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