Ammonia → HCID 59026683, compound

HRID 606054Notes

Reaction equation

HRID 606054 reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:29][O:30][CH2:31][CH3:32])[N:14]([CH2:15][CH2:16][CH2:17][C:18]3[O:22][N:21]=[C:20]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[CH:19]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:33]>CO>[CH2:31]([O:30][CH2:29][C:13]1[N:14]([CH2:15][CH2:16][CH2:17][C:18]2[O:22][N:21]=[C:20]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[CH:19]=2)[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:33])[C:11]=2[N:12]=1)[CH3:32]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86616876HCID 86616876, compound

Product 1

HCID 59026683HCID 59026683, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of 4-chloro-2-(ethoxymethyl)-1-[3-(3-pyridin-3-ylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline (1.78 g, 3.97 mmol) in a solution of 7 M ammonia in methanol (20 mL) was heated at 150° C. for 20 hours in a Parr pressure vessel. The volatiles were removed under reduced pressure and the resulting oil was partitioned between dichloromethane and 1 M KOH. The aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, gradient elution from 9:1 to 4:1 chloroform/CMA). After concentration of the appropriate fractions, a white solid was obtained. The white solid was triturated with diethyl ether and dried at 80° C. under vacuum to provide 2-(ethoxymethyl)-1-[3-(3-pyridin-3-ylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 199.0-200.0° C.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting oil was partitioned between dichloromethane and 1 M KOH
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (silica gel, gradient elution from 9:1 to 4:1 chloroform/CMA)
  9. customAfter concentration of the appropriate fractions, a white solid was obtained
  10. customThe white solid was triturated with diethyl ether
  11. customdried at 80° C. under vacuum

Sources & evidence

ORD record
ord-e7d93b33e2444c6fb14114f889ffceb4
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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