HCID 22254487, compound → HCID 23592062, compound

HRID 1839136Notes

Reaction equation

HRID 1839136 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][C:22]#[C:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[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>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[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

Participants

3

Reactant 1

HCID 22254487HCID 22254487, compound

Product 1

HCID 23592062HCID 23592062, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Methyl-1-{4-[(3-phenylprop-2-ynyl)oxy]butyl}-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.202 mmol) from Example 149 was combined with toluene (15 mL) in a Parr flask and heated to reflux. The resulting solution was purged with nitrogen. Palladium (1 g 10% palladium on carbon) was added to the solution under nitrogen, and the flask was pressurized with hydrogen at 310 kPa for 3 hours. Monitoring by HNMR indicated complete reaction. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was dissolved in dichloromethane and basified with 1 N potassium hydroxide to a pH of about 14. The layers were separated and the aqueous layer was extracted with dichloromethane (3×). The organic layers were combined, washed with 0.5 N potassium hydroxide (2×), water (3×), and brine (3×), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was recrystallized from acetonitrile, and the resulting shinny tan crystals were dried for 2 days, triturated with ether, collected by vacuum filtration, and dried to provide 0.5744 g of 2-methyl-1[4-(3-phenylpropoxy)butyl]-1H-imidazo[4,5-c]quinolin-4-amine, m.p. 105.1-106.0° C.

Workup

  1. temperatureheated to reflux
  2. customThe resulting solution was purged with nitrogen
  3. additionPalladium (1 g 10% palladium on carbon) was added to the solution under nitrogen
  4. customreaction
  5. filtrationThe catalyst was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. dissolutionThe concentrate was dissolved in dichloromethane and basified with 1 N potassium hydroxide to a pH of about 14
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted with dichloromethane (3×)
  10. washwashed with 0.5 N potassium hydroxide (2×), water (3×), and brine (3×)
  11. dry with materialdried with sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe resulting solid was recrystallized from acetonitrile
  15. customthe resulting shinny tan crystals were dried for 2 days
  16. customtriturated with ether
  17. filtrationcollected by vacuum filtration
  18. customdried

Sources & evidence

ORD record
ord-84025034f0c14728a9e31ca333ba0e69
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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