Ammonia → 2-(ethoxymethyl)-1-[(3-methyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 606035Notes

Reaction equation

HRID 606035 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:22][O:23][CH2:24][CH3:25])[N:14]([CH2:15][CH:16]3[O:20][N:19]=[C:18]([CH3:21])[CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:26]>CO>[CH2:24]([O:23][CH2:22][C:13]1[N:14]([CH2:15][CH:16]2[O:20][N:19]=[C:18]([CH3:21])[CH2:17]2)[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:26])[C:11]=2[N:12]=1)[CH3:25]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 866168704-chloro-2-(ethoxymethyl)-1-[(3-methyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

Product 1

HCID 116601182-(ethoxymethyl)-1-[(3-methyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

4-Chloro-2-(ethoxymethyl)-1-[(3-methyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline (1.30 g, 3.62 mmol) was treated with a solution of 7 M ammonia in methanol (60 mL), and the mixture was sealed in a pressure vessel and heated at 150° C. for 24 hours. The volatiles were removed under reduced pressure, and the residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The aqueous layer was extracted with two additional portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, gradient elution using 98:2 to 96:4 dichloromethane/methanol) to afford 2-(ethoxymethyl)-1-[(3-methyl-4,5-dihydroisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine (1.10 g) as a white solid that was crystallized from acetonitrile to provide white needles, mp 204-205° C.

Workup

  1. customthe mixture was sealed in a pressure vessel
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  4. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (silica gel, gradient elution using 98:2 to 96:4 dichloromethane/methanol)

Sources & evidence

ORD record
ord-b3fa047980204d19906fdb8f5ab62bc1
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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