O-Methylhydroxylamine hydrochloride → HCID 58869106, compound

HRID 1623137Notes

Reaction equation

HRID 1623137 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:25][CH2:26][CH3:27])[N:18]([CH2:19][CH2:20][CH2:21][C:22](=O)[CH3:23])[C:14]=2[C:13]2[CH:12]=[CH:11][C:10]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:9][C:8]=2[N:7]=1>C(O)C.O>[CH3:3][O:2][N:4]=[C:22]([CH2:21][CH2:20][CH2:19][N:18]1[C:14]2[C:13]3[CH:12]=[CH:11][C:10]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:9][C:8]=3[N:7]=[C:6]([NH2:5])[C:15]=2[N:16]=[C:17]1[CH2:25][CH2:26][CH3:27])[CH3:23]

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 69507151HCID 69507151, compound

Product 1

HCID 58869106HCID 58869106, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Methoxylamine hydrochloride (0.98 g, 11.79 mmol) was added to a solution of 5-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one (3.8 g, 9.83 mmol) in ethanol (50 mL) and water (10 mL) and stirred at ambient temperature for 3 hours. The mixture was then concentrated under reduced pressure, diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluting with 5% methanol in dichloromethane) and recrystallized from methanol and water to afford 3.6 g of 5-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one O-methyloxime as a tan solid, mp 191-192° C. MS (APCI) m/z 416.2 (M+H+); C25H29N5O

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additiondiluted with dichloromethane
  3. washwashed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel (eluting with 5% methanol in dichloromethane)
  7. customrecrystallized from methanol and water

Sources & evidence

ORD record
ord-1e909b7fcac9477681da4f408dad2f1e
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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