Sodium hydride → tert-Butyl{1-[2-(6-nitro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}carbamate

HRID 1644362Notes

Reaction equation

HRID 1644362 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[NH:9][C:8]=2[CH:14]=1)([O-:3])=[O:2].[H-].[Na+].CS(O[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26][CH2:25]1)(=O)=O.C(OC(=O)NC1CCN(CCN2C3C(=CC=C(OC)C=3)C=CC2=O)CC1)(C)(C)C>>[C:34]([O:33][C:31](=[O:32])[NH:30][CH:27]1[CH2:28][CH2:29][N:24]([CH2:23][CH2:22][N:9]2[C:8]3[CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=3[O:12][CH2:11][C:10]2=[O:13])[CH2:25][CH2:26]1)([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-one2×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 86642621tert-Butyl{1-[2-(6-nitro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}carbamateYield 98%

Procedure

6-Nitro-2H-1,4-benzoxazin-3(4H)-one (Intermediate 83) (776 mg, 4 mmol) was deprotonated with sodium hydride and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (5.6 mmol) as described for Intermediate 2. The product precipitated upon quenching of the reaction mixture with water and was isolated by filtration in 98% yield, yellow solid.

Workup

  1. customThe product precipitated
  2. customupon quenching of the reaction mixture with water
  3. customwas isolated by filtration in 98% yield, yellow solid

Sources & evidence

ORD record
ord-4479a6bc6e0245da8ad837329d6fd22a
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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