1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine → HCID 22180892, compound

HRID 583870Notes

Reaction equation

HRID 583870 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[CH:7]1>FC(F)(F)C(O)=O.[Pt](=O)=O>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[CH:7]1

Participants

4

Reactant 1

HCID 154537751-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 22180892HCID 22180892, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A catalytic amount of platinum (IV) oxide was added to a solution of 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine (2.75 g, 10.8 mmol) in trifluoroacetic acid (150 mL). The reaction mixture was placed under a hydrogen atmosphere at 50 psi (3.44×105 Pa). After 1 week analysis by mass spectroscopy indicated the presence of both starting material and the tetrahydro product. Fresh catalyst was added to the reaction mixture and hydrogenation was continued at 50 psi (3.44×105 Pa). After 2 weeks the reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under vacuum. The residue was dissolved in 1N hydrochloric acid (120 mL) and the solution was stirred at ambient temperature for 1 hour. The solution was made basic (pH 10) by the addition of 50% sodium hydroxide and then extracted with dichloromethane (5×100 mL). The extracts were combined and concentrated under vacuum to provide 2.08 g of 1-(4-aminobutyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a white solid.

Workup

  1. waitAfter 1 week analysis by mass spectroscopy indicated
  2. additionFresh catalyst was added to the reaction mixture and hydrogenation
  3. filtrationAfter 2 weeks the reaction mixture was filtered
  4. customto remove the catalyst
  5. concentrationThe filtrate was concentrated under vacuum
  6. dissolutionThe residue was dissolved in 1N hydrochloric acid (120 mL)
  7. additionby the addition of 50% sodium hydroxide
  8. extractionextracted with dichloromethane (5×100 mL)
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f5e8e0e94e19425fbf1bf9aa48f40eb9
Source dataset
uspto-grants-2005_08
Patent number
US06924293B2

Reaction notes

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