Acetic Acid → HCID 86612245, compound

HRID 1623096Notes

Reaction equation

HRID 1623096 reaction equation
C([BH3-])#N.[Na+].C(O)(=O)C.[CH3:9][O:10][N:11]=[CH:12][CH2:13][CH2:14][CH2:15][N:16]1[C:28]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[C:20]([NH2:29])[C:19]=2[N:18]=[C:17]1[CH2:30][CH2:31][CH3:32]>CO>[CH3:9][O:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:28]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[C:20]([NH2:29])[C:19]=2[N:18]=[C:17]1[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 86612244HCID 86612244, compound

Product 1

HCID 86612245HCID 86612245, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (0.54 g, 8.64 mmol, 3 eq) and acetic acid (7 mL) were added to a solution of 4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyraldehyde O-methyloxime (0.94 g, 2.88 mmol, 1 eq) in methanol (7 mL) and stirred at ambient temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure and diluted with dichloromethane (60 mL) and saturated aqueous sodium bicarbonate (40 mL). The phases were separated and the aqueous phase was adjusted to pH ˜8 with solid sodium bicarbonate and extracted with dichloromethane (2×20 mL). The combined organics were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to provide 1.01 g of 1-[4-(methoxyamino)butyl]-2-propyl-1H-imidazo[4,5-c]-1,5-naphthyridin-4-amine as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with dichloromethane (60 mL) and saturated aqueous sodium bicarbonate (40 mL)
  3. customThe phases were separated
  4. extractionextracted with dichloromethane (2×20 mL)
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e58022b6cdc4931af8689e4b05feee5
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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