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

HRID 1798882Notes

Reaction equation

HRID 1798882 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-c7b62552090149a390e93c43e644d9f2
Source dataset
uspto-grants-2013_01
Patent number
US08343993B2

Reaction notes

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