Water → HCID 11956299, compound

HRID 2426372Notes

Reaction equation

HRID 2426372 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][NH:10][O:11][CH3:12].Cl[CH2:14][C:15]1[N:16]([CH2:29][C:30]([OH:33])([CH3:32])[CH3:31])[C:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[C:19]([NH2:27])[C:18]=2[N:28]=1.O>CN(C=O)C>[OH:33][C:30]([CH3:32])([CH3:31])[CH2:29][N:16]1[C:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[C:19]([NH2:27])[C:18]=2[N:28]=[C:15]1[CH2:14][N:10]([O:11][CH3:12])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 67052320HCID 67052320, compound

Product 1

HCID 11956299HCID 11956299, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Triethylamine (0.747 g, 1.03 mL, 7.38 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.480 g, 4.92 mmol) were added to a stirring suspension of 2-chloromethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.750 g, 2.46 mmol) in DMF (5 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 (100 mL). A solid was removed by filtration and discarded. The filtrate was extracted with ethyl acetate (3×100 mL). The combined organic fractions were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using a HORIZON HPFC system (silica cartridge, eluting with 5-20% methanol in dichloromethane). The resulting oil was crystallized from dichloromethane and isolated by filtration to yield 132 mg of 1-(2-Hydroxy-2-methylpropyl)-2-{[methoxy(methyl)amino]methyl}-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 220-222° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customA solid was removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washa HORIZON HPFC system (silica cartridge, eluting with 5-20% methanol in dichloromethane)
  9. customThe resulting oil was crystallized from dichloromethane
  10. customisolated by filtration

Sources & evidence

ORD record
ord-ec1c1754aaa84760988f2e406f729466
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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