HCID 22254496, compound → HCID 22254418, compound

HRID 1611800Notes

Reaction equation

HRID 1611800 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][CH2:17][CH2:18][O:19][CH2:20][C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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.[H][H]>[Pd].C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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

5

Reactant 2

HCID 22254496HCID 22254496, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22254418HCID 22254418, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

2-Methyl-1-{3-[(3-phenylprop-2-ynyl)oxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine (1.4 g, 3.779 mmol) was combined with toluene (15 mL) in a Parr flask and heated to reflux. The resulting solution was cooled to room temperature and purged with nitrogen. Palladium (0.6 g 10% palladium on carbon) was added to the solution under nitrogen, and the flask was pressurized with hydrogen at 310 kPa for 2.75 hours. Monitoring by HNMR indicated incomplete reaction. More 10% palladium on carbon (0.16 g) was added, and after an additional 2.5 hours at 310 kPA of hydrogen, the reaction was determined to be complete. The catalyst was filtered off, and the volatiles were removed under reduced pressure. The resulting white solid was recrystallized from acetonitrile and dried for 5 days to provide 1.0723 g of 2-methyl-1-[3-(3-phenylpropoxy)propyl]-1H-imidazo[4,5-c]quinolin-4-amine, m.p. 145.0-146.1° C.

Workup

  1. temperatureheated to reflux
  2. custompurged with nitrogen
  3. additionPalladium (0.6 g 10% palladium on carbon) was added to the solution under nitrogen
  4. customreaction
  5. filtrationThe catalyst was filtered off
  6. customthe volatiles were removed under reduced pressure
  7. customThe resulting white solid was recrystallized from acetonitrile
  8. customdried for 5 days

Sources & evidence

ORD record
ord-a50a631fc2aa4293b4878a85753d0e92
Source dataset
uspto-grants-2006_01
Patent number
US06989389B2

Reaction notes

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