Sodium Hydroxide → HCID 86612243, compound

HRID 1623094Notes

Reaction equation

HRID 1623094 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[OH-].[Na+].[CH2:7]([C:10]1[N:11]([CH2:23][CH2:24][CH2:25][CH:26]=O)[C:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1)[CH2:8][CH3:9]>CO>[CH3:3][O:2][N:4]=[CH:26][CH2:25][CH2:24][CH2:23][N:11]1[C:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=[C:10]1[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86052837HCID 86052837, compound

Product 1

HCID 86612243HCID 86612243, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methoxylamine hydrochloride (3.39 g, 40.6 mmol, 2 eq) and 6M sodium hydroxide solution (7.5 mL, 44.7 mmol. 2.2 eq) were added sequentially to a solution of 4-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyraldehyde (5.73 g, 20.3 mmol, 1 eq) in methanol (80 mL) and stirred overnight. The mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (100 mL) and water (60 mL). The pH of the mixture was adjusted to 7 and the layers were separated. The aqueous layer was extracted with dichloromethane (2×20 mL) and the combined organics were washed with brine (75 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 6.45 g of 4-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyraldehyde O-methyloxime as an orange oil with an E/Z ratio of 77:23. The material was used in subsequent steps without any further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (100 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with dichloromethane (2×20 mL)
  5. washthe combined organics were washed with brine (75 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-377dc8afa2bb49688fde5a11d29b50ab
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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