m-Chloroperbenzoic acid → HCID 69506838, compound

HRID 2366699Notes

Reaction equation

HRID 2366699 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:29][CH2:30][CH2:31][C:32]([NH2:34])=[O:33])[C:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:28]=1)[CH3:13]>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:29][CH2:30][CH2:31][C:32]([NH2:34])=[O:33])[C:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N+:21]([O-:9])=[CH:20][C:19]=2[N:28]=1)[CH3:13]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 57447077HCID 57447077, compound

Product 1

HCID 69506838HCID 69506838, compoundYield 136.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

mCPBA (1.80 g, 7.28 mmol) was added to a solution of 4-[2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butanamide (1.63 g, 5.20 mmol) in chloroform (50 mL); the reaction was stirred for three hours at ambient temperature. An analysis by LC/MS indicated the reaction was incomplete; therefore, additional mCPBA (1.2 equivalents) was added. The reaction was stirred for two hours and then diluted with saturated aqueous sodium bicarbonate (75 mL) and chloroform (75 mL). The aqueous layer was extracted with dichloromethane (2×30 mL) and chloroform (12×20 mL), and the combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 2.34 g of 4-[2-(ethoxymethyl)-5-oxido-1H-imidazo[4,5-c][ 1,5]naphthyridin-1-yl]butanamide as an orange solid.

Workup

  1. stirringThe reaction was stirred for two hours
  2. extractionThe aqueous layer was extracted with dichloromethane (2×30 mL) and chloroform (12×20 mL)
  3. dry with materialthe combined organic fractions were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74856cecb84c4948bc024dd50f2fd748
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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