HCID 22320528, compound → HCID 68538661, compound

HRID 1992617Notes

Reaction equation

HRID 1992617 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1>FC(F)(F)C(O)=O.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 22320528HCID 22320528, compound

Product 1

HCID 68538661HCID 68538661, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Platinum (IV) oxide (3.5 g) was added to a solution of 4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (prepared as described in Example 9 of U.S. Pat. No. 6,664,264, 4.00 g, 15.6 mmol) in trifluoroacetic acid (200 mL), and the mixture was shaken under hydrogen pressure for 2 days on a Parr apparatus. The reaction mixture was concentrated under reduced pressure, carefully diluted with methanol, and filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure. The resulting residue was diluted with a solution of 4 M hydrogen chloride in 1,4-dioxane (100 mL) and stirred at ambient temperature for 1 hour, and then 4 M aqueous sodium hydroxide was added to adjust to pH 13. The mixture was transferred to a separatory funnel, and dichloromethane was added. The mixture was shaken and allowed to stand overnight at ambient temperature. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 1.0 g of 4-(4-amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol as a white solid.

Workup

  1. customprepared
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additioncarefully diluted with methanol
  4. filtrationfiltered through a layer of CELITE filter agent
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionThe resulting residue was diluted with a solution of 4 M hydrogen chloride in 1,4-dioxane (100 mL)
  7. addition4 M aqueous sodium hydroxide was added
  8. customThe mixture was transferred to a separatory funnel
  9. additiondichloromethane was added
  10. stirringThe mixture was shaken
  11. waitto stand overnight at ambient temperature
  12. customThe organic layer was separated
  13. extractionthe aqueous layer was extracted with dichloromethane
  14. dry with materialdried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-269d06da9a534feb8cf0fc597ec39ece
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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