Water → HCID 73152965, compound

HRID 2426357Notes

Reaction equation

HRID 2426357 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:24][CH2:25][C:26](=O)[CH3:27])[N:18]([CH2:19][C:20]([OH:23])([CH3:22])[CH3:21])[C:14]=2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1.O>N1C=CC=CC=1>[CH3:3][O:2][N:4]=[C:26]([CH2:25][CH2:24][C:17]1[N:18]([CH2:19][C:20]([OH:23])([CH3:22])[CH3:21])[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:5])[C:15]=2[N:16]=1)[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 521874O-Methylhydroxylamine hydrochlorideHCID 67052308HCID 67052308, compound

Product 1

HCID 73152965HCID 73152965, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxylamine hydrochloride (0.26 g, 3.1 mmol) was added to a stirred solution of 4-[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]butan-2-one (0.600 g, 1.84 mmol) in pyridine (9 mL), and the reaction was stirred at room temperature for 45 minutes. Water (50 mL) was added. The aqueous layer was separated, extracted with dichloromethane (2×50 mL), adjusted to pH 10 with the addition of saturated aqueous sodium carbonate, and extracted with dichloromethane (2×25 mL). The combined organic fractions were washed sequentially with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting white powder was stirred with diethyl ether for one hour, isolated by filtration, and washed with diethyl ether. The resulting solid (0.45 g) was recrystallized from acetonitrile (20 mL), and the crystals were isolated by filtration, washed with acetonitrile, and dried for 15 hours under vacuum at 60° C. to provide 0.40 g of 4-[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]butan-2-one O-methyloxime as white needles, mp 182-184° C.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with dichloromethane (2×50 mL)
  3. additionadjusted to pH 10 with the addition of saturated aqueous sodium carbonate
  4. extractionextracted with dichloromethane (2×25 mL)
  5. washThe combined organic fractions were washed sequentially with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. stirringThe resulting white powder was stirred with diethyl ether for one hour
  10. customisolated by filtration
  11. washwashed with diethyl ether
  12. customThe resulting solid (0.45 g) was recrystallized from acetonitrile (20 mL)
  13. customthe crystals were isolated by filtration
  14. washwashed with acetonitrile
  15. customdried for 15 hours under vacuum at 60° C.

Sources & evidence

ORD record
ord-67b6f92bfc32417a866f7e49ace19957
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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