N-[2-(4-Amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamide → N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamide

HRID 2383195Notes

Reaction equation

HRID 2383195 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:23][O:24][CH2:25][CH3:26])[N:14]([CH2:15][C:16]([NH:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:27]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]([CH2:23][O:24][CH2:25][CH3:26])[N:14]([CH2:15][C:16]([NH:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:27])=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 11719566N-[2-(4-Amino-7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 136075202N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamideYield 39.7%

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]acetamide (0.72 g, 1.56 mmol) was dissolved in 200 mL of warm ethanol. 10% Palladium on carbon (0.33 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 filtrate was removed under reduced pressure. The resulting brown solid was purified by flash column chromatography on silica gel, eluting with 14% methanol in dichloromethane. The fractions containing the desired product were combined and further purified by column chromatography on a HORIZON HPFC system. A silica gel cartridge was used with the eluent being a gradient of 30-50% CMA in chloroform. The clean fractions were combined and concentrated under reduced pressure to provide 0.23 g of N-[2-(4-amino-2-ethoxymethyl-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]acetamide as an off-white solid, m.p. 140° C.

Workup

  1. filtrationThe reaction was filtered through CELITE
  2. filtrationfilter agent
  3. customthe filtrate was removed under reduced pressure
  4. customThe resulting brown solid was purified by flash column chromatography on silica gel
  5. washeluting with 14% methanol in dichloromethane
  6. additionThe fractions containing the desired product
  7. customfurther purified by column chromatography on a HORIZON HPFC system
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5427dc7e6bed4980823ad7fe7f179897
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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