HCID 57545297, compound → HCID 136075197, compound

HRID 2383198Notes

Reaction equation

HRID 2383198 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:26][O:27][CH2:28][CH3:29])[N:14]([CH2:15][C:16]([NH:19][C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:30]CC3C=CC=CC=3)=[CH:5][C:4]=2[N:3]=1.[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:26][O:27][CH2:28][CH3:29])[N:14]([CH2:15][C:16]([NH:19][C:20]([NH:22][CH:23]([CH3:24])[CH3:25])=[O:21])([CH3:17])[CH3:18])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:30])=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 57545297HCID 57545297, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136075197HCID 136075197, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[2-(4-Amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N′-isopropylurea (0.94 g, 1.66 mmol) was dissolved in 100 mL of warm ethanol and then cooled back to ambient temperature. 10% Palladium on carbon (0.35 g) was added and the mixture was shaken overnight under 50 psi (3.4×105 Pa) of hydrogen. The reaction was filtered through CELITE filter agent, and the filter pad was washed sequentially with ethanol and methanol. The filtrate was concentrated under reduced pressure. The resulting off white solid was purified by flash column chromatography on silica gel (eluting with 90:10:1 dichloromethane/methanol/aqueous ammonium hydroxide) to provide 0.53 g of N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N′-isopropylurea as an off-white powder, m.p. 163-168° C.

Workup

  1. filtrationThe reaction was filtered through CELITE
  2. filtrationfilter agent
  3. washthe filter pad was washed sequentially with ethanol and methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resulting off white solid was purified by flash column chromatography on silica gel (eluting with 90:10:1 dichloromethane/methanol/aqueous ammonium hydroxide)

Sources & evidence

ORD record
ord-6f8295531d30489281d05434eeceec16
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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