HCID 22254449, compound → HCID 22254483, compound

HRID 1611798Notes

Reaction equation

HRID 1611798 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:11]([NH2:20])[C:10]=2[N:9]=[C:8]1[CH3:21])(=O)C>FC(F)(F)C(O)=O>[NH2:20][C:11]1[C:10]2[N:9]=[C:8]([CH3:21])[N:7]([CH2:6][CH2:5][OH:4])[C:19]=2[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[N:12]=1

Participants

3

Reactant 1

HCID 22254449HCID 22254449, compound

Product 1

HCID 22254483HCID 22254483, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A Parr flask was charged with 2-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl acetate (3.61 g, 12.64 mmol), trifluoroacetic acid (50 mL) and purged with nitrogen. To this solution was added platinum(IV) oxide (0.5 g). The reaction was judged to be complete after 13 days of hydrogenation at ambient temperature. The solution was filtered and the volatiles removed under reduced pressure. The resulting brown oil was partitioned between dichloromethane and saturated aqueous sodium bicarbonate to a pH of ˜8. The layers were separated. The aqueous layer was extracted with dichloromethane (4×). The organic fractions were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting white solid was purified by recrystallization from ethyl acetate/methanol (9/1) and dried to provide 0.98 g of 2-(4-amino-2-methyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)ethanol as a white solid.

Workup

  1. custompurged with nitrogen
  2. additionTo this solution was added platinum(IV) oxide (0.5 g)
  3. filtrationThe solution was filtered
  4. customthe volatiles removed under reduced pressure
  5. customThe resulting brown oil was partitioned between dichloromethane and saturated aqueous sodium bicarbonate to a pH of ˜8
  6. customThe layers were separated
  7. extractionThe aqueous layer was extracted with dichloromethane (4×)
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting white solid was purified by recrystallization from ethyl acetate/methanol (9/1)
  11. customdried

Sources & evidence

ORD record
ord-66ac2f427abc45e1b24108396a7a48ef
Source dataset
uspto-grants-2006_01
Patent number
US06989389B2

Reaction notes

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