Water → HCID 178508172, compound

HRID 2426373Notes

Reaction equation

HRID 2426373 reaction equation
C(N(CC)CC)C.Cl.O(N)C.ClC[C:14]1[N:15](CC(O)(C)C)[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[C:18]([NH2:26])[C:17]=2[N:27]=1.O>CN(C=O)C>[NH:15]1[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[C:18]([NH2:26])[C:17]=2[N:27]=[CH:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 67052320HCID 67052320, compound

Product 1

HCID 178508172HCID 178508172, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Triethylamine (1.49 g, 2.1 mL, 14.8 mmol) and methoxylamine hydrochloride (0.822 g, 9.84 mmol) were added to a stirring suspension of 2-chloromethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.50 g, 4.92 mmol) in DMF (10 mL). The resulting suspension was heated to 50° C. and stirred for 17 hours. The reaction mixture was cooled to room temperature and poured into water (20 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL) and dichloromethane (3×50 mL). A significant amount of the desired product remained in the aqueous layer thus the organic fractions were combined with the aqueous fraction and concentrated under reduced pressure. The residue was purified by column chromatography using a HORIZON HPFC system (silica cartridge, eluting with 10-25% methanol in dichloromethane) and triturated with dichloromethane to provide 760 mg of 1-(2-Hydroxy-2-methylpropyl)-2-{[methoxylamino]methyl)}-1H-imidazo[4,5-c]quinolin-4-amine; hydrochloride as a tan solid, mp 255-257° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL) and dichloromethane (3×50 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washa HORIZON HPFC system (silica cartridge, eluting with 10-25% methanol in dichloromethane)
  6. customtriturated with dichloromethane

Sources & evidence

ORD record
ord-0a4be634225a46e7b3972d8e9554e014
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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