Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate → methyl 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate

HRID 244824Notes

Reaction equation

HRID 244824 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6](/[CH:24]=[CH:25]/[C:26]([O:28][CH3:29])=[O:27])=[CH:5][C:4]=2[N:3]=1>[Pd].CO>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 57657222Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate

Product 1

HCID 57657269methyl 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A glass Parr vessel was charged with 10% palladium on carbon catalyst (0.35 g, 0.1 eq. weight/weight (w/w)), methanol (50 mL) ethanol (50 ml) and Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate (3.5 g, 8.8 mmol). The vessel was evacuated and charged with hydrogen gas (45 psi, 3.1×105 Pa). The reaction was shaken at ambient temperature overnight (approximately 18 hours). The reaction mixture was filtered to remove the catalyst and concentrated to dryness. The crude product was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 0-30% CMA in chloroform) followed by recrystallization from acetonitrile to provide methyl 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate as a white solid.

Workup

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (45 psi, 3.1×105 Pa)
  3. filtrationThe reaction mixture was filtered
  4. customto remove the catalyst
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by chromatography
  7. washa HORIZON HPFC system (silica cartridge, eluting with 0-30% CMA in chloroform)
  8. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-076cf6e7e686498e9d0484394d908a92
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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