Sodium Carbonate → [1-(2-fluoro-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl acetate

HRID 81936Notes

Reaction equation

HRID 81936 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:7]([CH2:19][C:20]([F:23])([CH3:22])[CH3:21])[C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)(=[O:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:29].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]1[N:7]([CH2:19][C:20]([F:23])([CH3:22])[CH3:21])[C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N+:11]([O-:29])=[CH:10][C:9]=2[N:18]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 68933078HCID 68933078, compound

Product 1

HCID 68935317[1-(2-fluoro-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl acetateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[1-(2-Fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl acetate (1.59 g, 5.03 mmol) was dissolved in 50 mL of CH2Cl2 and treated with 3-chloroperoxybenzoic acid (1.52 g, 57-86% purity). After stirring for 2 hours, the reaction mixture was treated with 25 mL of CH2Cl2 and 20 mL of 5% Na2CO3 solution and the layers were separated. The organic layer was washed with H2O (20 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give 1.67 g of [1-(2-fluoro-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl acetate as an off-white solid.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with H2O (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6f548510c834bc1a0eba16e98c3f401
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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