Sodium Carbonate → HCID 68934933, compound

HRID 81939Notes

Reaction equation

HRID 81939 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:24][C:25]([F:28])([CH3:27])[CH3:26])[C:13]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:34].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:24][C:25]([F:28])([CH3:26])[CH3:27])[C:13]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:16]([O-:34])=[CH:15][C:14]=2[N:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 689332372-[2-(Benzyloxy)ethyl]-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridine

Product 1

HCID 68934933HCID 68934933, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[2-(Benzyloxy)ethyl]-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridine (1.89 g, 5.0 mmol) was dissolved in 50 mL of CH2Cl2 and treated with 3-chloroperoxybenzoic acid (1.50 g, 57-86% purity). After stirring for 2 hours, the reaction mixture was treated with 50 mL of 2% Na2CO3 solution and the layers were separated. The aqueous portion was extracted with an additional 25 mL of CH2Cl2. The combined organic layers were washed successively with 2% Na2CO3, H2O and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give 1.97 g of 2-[2-(benzyloxy)ethyl]-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridine 5-oxide as an off-white solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous portion was extracted with an additional 25 mL of CH2Cl2
  3. washThe combined organic layers were washed successively with 2% Na2CO3, H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4578162880e14eac919c5647459d20be
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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