Trifluoroacetic acid → HCID 10149351, compound

HRID 599448Notes

Reaction equation

HRID 599448 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][OH:20])[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[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.[H][H]>ClCCl.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][OH:20])[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9856687HCID 9856687, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10149351HCID 10149351, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of [4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methanol (15.2 g, 56.2 mmol, U.S. Pat. No. 5,389,640 Example 9), platinum(IV) oxide (7.6 g), and trifluoroacetic acid (75 mL) was hydrogenated at 50 psi (3.5×105 Pa) of hydrogen on a Parr apparatus for 2 days. The mixture was diluted with dichloromethane and filtered through CELITE filter agent, which was rinsed afterwards with dichloromethane and methanol. The filtrate was concentrated under reduced pressure and the residue was partitioned between dichloromethane (250 mL) and 1:1 saturated aqueous sodium bicarbonate/water (250 mL). Some solid formed that was isolated by filtration. The aqueous layer was extracted with dichloromethane (2×200 mL). The solid was dissolved in methanol and the resulting solution was combined with the organic layers, concentrated under reduced pressure, and purified by chromatography using a HORIZON HPFC system (silica gel, elution with 10% 1 M NH3 in methanol/dichloromethane) to afford 4.98 g of [4-amino-1-(2-methylpropyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-2-yl]methanol as a grey solid.

Workup

  1. filtrationfiltered through CELITE
  2. filtrationfilter agent, which
  3. washwas rinsed afterwards with dichloromethane and methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was partitioned between dichloromethane (250 mL) and 1:1 saturated aqueous sodium bicarbonate/water (250 mL)
  6. customSome solid formed that
  7. customwas isolated by filtration
  8. extractionThe aqueous layer was extracted with dichloromethane (2×200 mL)
  9. dissolutionThe solid was dissolved in methanol
  10. concentrationconcentrated under reduced pressure
  11. custompurified by chromatography
  12. washa HORIZON HPFC system (silica gel, elution with 10% 1 M NH3 in methanol/dichloromethane)

Sources & evidence

ORD record
ord-98bb3e2c070b4de1854b04472c62f137
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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