HCID 57545309, compound → HCID 57545340, compound

HRID 2383208Notes

Reaction equation

HRID 2383208 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:28][O:29][CH2:30][CH3:31])[N:14]([CH2:15][C:16]([NH:19][C:20]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[C:7]([O:32]CC3C=CC=CC=3)[CH:6]=[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]([CH2:28][O:29][CH2:30][CH3:31])[N:14]([CH2:15][C:16]([NH:19][C:20]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])([CH3:17])[CH3:18])[C:10]=2[C:9]2[CH:8]=[C:7]([OH:32])[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 57545309HCID 57545309, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 57545340HCID 57545340, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

N-{2-[4-Amino-8-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}cyclohexanecarboxamide (1.25 g, 2.36 mmol) was dissolved in 40 mL of ethanol and 10% palladium on carbon (0.58 g) was added. The mixture was shaken overnight under 50 psi (3.4×105 Pa) of hydrogen. An additional 0.21 g of 10% palladium on carbon was added and the reaction was shaken under 50 psi (3.4×105 Pa) of hydrogen for three more hours. The reaction was filtered through CELITE filter agent, and the filter cake was washed with 100 mL of ethanol. The filtrate was concentrated under reduced pressure. The resulting off white solid was purified by column chromatography on a HORIZON HPFC system. A silica gel cartridge was used eluting with a gradient of 10-30% CMA in chloroform to provide 0.56 g of N-{2-[4-amino-8-hydroxy-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}cyclohexanecarboxamide as a white powder, m.p. 231-232° C.

Workup

  1. filtrationThe reaction was filtered through CELITE
  2. filtrationfilter agent
  3. washthe filter cake was washed with 100 mL of ethanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resulting off white solid was purified by column chromatography on a HORIZON HPFC system
  6. washA silica gel cartridge was used eluting with a gradient of 10-30% CMA in chloroform

Sources & evidence

ORD record
ord-73e17da5215a494f97f80bbfbfd32428
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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