Sodium Carbonate → HCID 178467656, compound

HRID 1924034Notes

Reaction equation

HRID 1924034 reaction equation
[Si](OCC[N:11]1[C:23]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:13]=[C:12]1[CH2:24][O:25][CH2:26][CH3:27])(C(C)(C)C)(C)C.ClC1C=CC=C(C(OO)=[O:36])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:26]([O:25][CH2:24][C:12]1[NH:11][C:23]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:16]([O-:36])=[CH:15][C:14]=2[N:13]=1)[CH3:27]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67521562HCID 67521562, compound

Product 1

HCID 178467656HCID 178467656, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridine (2.30 g, 5.96 mmol) was dissolved in 30 mL of CH2Cl2 and treated with meta-chloroperbenzoic acid (MCPBA) (1.80 g, 57-86% purity). After stirring for 2 hours, the reaction mixture was treated with 25 mL of CH2Cl2 and 25 mL of 5% Na2CO3 solution and the layers were separated. The organic portion was then washed successively with H2O (20 mL) and brine (20 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to give 2.40 g of 1-2-{[tert-butyl(dimethyl)silyl]oxy)ethyl}-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridine 5-oxide as a purple syrup.

Workup

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

Sources & evidence

ORD record
ord-2082851f47c041148f87813c4454366a
Source dataset
uspto-grants-2012_05
Patent number
US08178539B2

Reaction notes

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