Sodium hydride → HCID 86642629, compound

HRID 1644383Notes

Reaction equation

HRID 1644383 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C:11](=[O:14])[NH:10][C:9]=2[CH:15]=1)(=[O:4])=[O:3].[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>ClCCl.CO>[C:35]([O:34][C:32](=[O:33])[NH:31][CH:28]1[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][N:10]2[C:9]3[CH:15]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=3[O:13][CH2:12][C:11]2=[O:14])[CH2:26][CH2:27]1)([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 4594979HCID 4594979, compound2×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 86642629HCID 86642629, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

6-(Methylsulfonyl)-2H-1,4-benzoxazin-3(4H)-one (Intermediate 101) (280 mg, 1.23 mmol) was deprotonated with sodium hydride and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (1.62 mmol) as described for Intermediate 2. Chromatography on silica gel with dichloromethane/methanol (20:1) gave the product in 66% yield as a yellow gum.

Sources & evidence

ORD record
ord-7981a4e908534fb4b8bc6e08b1aace28
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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