Methanol → HCID 69080343, compound

HRID 244843Notes

Reaction equation

HRID 244843 reaction equation
CO.[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:22][CH3:23])[N:16]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][C:8]([CH:24]=[CH:25][C:26]([O:28][CH3:29])=[O:27])=[CH:7][C:6]=2[N:5]=1>[Pd].C(O)C>[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:22][CH3:23])[N:16]([CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][C:8]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:7][C:6]=2[N:5]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 69083060HCID 69083060, compound

Product 1

HCID 69080343HCID 69080343, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A glass Parr vessel was charged with 10% palladium on carbon (1.0 g), methanol (75 mL), ethanol (75 mL) and methyl 3-[4-amino-2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate (approximately 4 g, 10.8 mmol). The vessel was evacuated and charged with hydrogen gas (40 psi, 2.8×105 Pa). The mixture was shaken at 50° C. for approximately 18 hours. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated under reduced pressure to provide 3.55 g of methyl 3-[4-amino-2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanate as an off-white solid. MS (ESI) m/z 371 (M+H)+.

Workup

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (40 psi, 2.8×105 Pa)
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-10db0e7a774e41d8b6b23f3a23725b0f
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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