Sodium Hydroxide → HCID 86612255, compound

HRID 1623124Notes

Reaction equation

HRID 1623124 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:25][O:26][CH2:27][CH3:28])[N:18]([CH2:19][CH2:20][CH2:21][C:22](=O)[CH3:23])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1.[C:29]([BH3-])#N.[Na+].[OH-].[Na+]>O.C(O)C.C(O)(=O)C>[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:25][O:26][CH2:27][CH3:28])[N:18]([CH2:19][CH2:20][CH2:21][CH:22]([NH:4][O:2][CH2:3][CH3:29])[CH3:23])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 58837337HCID 58837337, compound

Product 1

HCID 86612255HCID 86612255, compoundYield 68.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Methoxylamine hydrochloride (0.25 g, 3.0 mmol) in water (4 mL) was added to a solution of 5-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one (0.81 g, 2.5 mmol) in ethanol (25 mL) and stirred at ambient temperature for 3 hours. Addition of acetic acid (20 mL) and sodium cyanoborohydride (2.0 g, 32 mmol) to the reaction mixture followed. After 2.5 hours, the reaction mixture was cooled to 0° C. and the pH was adjusted to ˜8 with 25% sodium hydroxide solution. The mixture was concentrated under reduced pressure, diluted with dichloromethane (75 mL) and saturated aqueous sodium bicarbonate and the layers were separated. The combined organic layers were washed with water (25 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford 0.64 g of N-[4-(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-methylbutyl]-O-ethylhydroxylamine.

Workup

  1. waitAfter 2.5 hours
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additiondiluted with dichloromethane (75 mL) and saturated aqueous sodium bicarbonate
  5. customthe layers were separated
  6. washThe combined organic layers were washed with water (25 mL)
  7. dry with materialdried over potassium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd2db0bb75e740e095b2db2236ac7de5
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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