HCID 57550527, compound → HCID 57550541, compound

HRID 1097579Notes

Reaction equation

HRID 1097579 reaction equation
[NH2:1][C:2]1[N:3]([CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:14])[C:5]=2[N:15]=1>[Pt](=O)=O.FC(F)(F)C(O)=O>[NH2:1][C:2]1[N:3]([CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[C:4]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[N:7]=[C:6]([NH2:14])[C:5]=2[N:15]=1

Participants

4

Reactant 1

HCID 57550527HCID 57550527, compound

Product 1

HCID 57550541HCID 57550541, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

1-(2,4-Diamino-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (0.50 g, 1.8 mmol), trifluoroacetic acid (200 mL), and platinum (IV) oxide (300 mg) were added to a Parr vessel and shaken under hydrogen pressure (45 psi, 3.1×105 Pa) for eight days. The volatiles were removed under reduced pressure, and the residue was dissolved in methanol and filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure, and the resulting solid was dissolved in methanol. Hydrogen chloride (30 mL of a 4 M solution in dioxane) was added, and the resulting solution was stirred for two hours. Ammonia (7 M in methanol) was added, and the volatiles were then removed under reduced pressure. Ammonia (7 M in methanol was added a second time, and the resulting mixture was concentrated under reduced pressure. The residue was purified by automated flash chromatography (silica cartridge, eluting with 0-8% methanol in dichloromethane with aqueous ammonium hydroxide added). The resulting white solid was washed with hot acetonitrile and dried in a vacuum oven to provide 280 mg of 1-(2,4-diamino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as a white solid, mp >270° C.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in methanol
  3. filtrationfiltered through a layer of CELITE filter agent
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionthe resulting solid was dissolved in methanol
  6. additionHydrogen chloride (30 mL of a 4 M solution in dioxane) was added
  7. stirringthe resulting solution was stirred for two hours
  8. additionAmmonia (7 M in methanol) was added
  9. customthe volatiles were then removed under reduced pressure
  10. additionAmmonia (7 M in methanol was added a second time
  11. concentrationthe resulting mixture was concentrated under reduced pressure
  12. customThe residue was purified by automated flash chromatography (silica cartridge, eluting with 0-8% methanol in dichloromethane with aqueous ammonium hydroxide added)
  13. washThe resulting white solid was washed with hot acetonitrile
  14. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d5d91d1243c14c8ab2c55da8775d96e0
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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