O-Methylhydroxylamine hydrochloride → HCID 86612268, compound

HRID 1623208Notes

Reaction equation

HRID 1623208 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[CH2:5]([C:8]1[N:9]([CH2:21][CH2:22][CH2:23][C:24](=O)[CH3:25])[C:10]2[C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:20]=1)[CH2:6][CH3:7]>CO>[CH3:3][O:2][N:4]=[C:24]([CH2:23][CH2:22][CH2:21][N:9]1[C:10]2[C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:20]=[C:8]1[CH2:5][CH2:6][CH3:7])[CH3:25]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 69507057HCID 69507057, compound

Product 1

HCID 86612268HCID 86612268, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methoxylamine hydrochloride (2.23 g, 26.7 mmol) was added to a solution of 5-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one (6.06 g of crude material prepared as described in Parts A and B of Example 22) in methanol (80 mL). The reaction mixture was stirred at room temperature for 48 hours and then concentrated under reduced pressure. The residue was dissolved dichloromethane (60 mL) and the pH was adjusted to 8 by the addition of saturated aqueous sodium bicarbonate (40 mL) and then solid sodium bicarbonate. The layers were separated and the aqueous layer was extracted with dichloromethane (30 mL). The combined organics were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to afford 6.33 g of 5-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one O-methyloxime a yellow oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved dichloromethane (60 mL)
  3. additionthe pH was adjusted to 8 by the addition of saturated aqueous sodium bicarbonate (40 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane (30 mL)
  6. dry with materialThe combined organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-709d6485ccd44c7796975e430affa128
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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