Sodium Bicarbonate → HCID 57447097, compound

HRID 2366711Notes

Reaction equation

HRID 2366711 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:25]2CCOCC2)=[O:24])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9](N)[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4].C([O-])(=O)C.[NH4+].C(=O)(O)[O-].[Na+]>>[CH2:1]([C:5]1[N:6]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=[O:24])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 57447085HCID 57447085, compound

Product 1

HCID 57447097HCID 57447097, compoundYield 94%

Conditions

Temperature
130 °C

Procedure

Ethyl 5-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate (10.0 g, 28.2 mmol, prepared in Example 46) and ammonium acetate (10 g) were sealed in a high-pressure vessel, heated for two days at 130° C., and then allowed to cool to ambient temperature. Saturated aqueous sodium bicarbonate was added, and the mixture was then extracted with dichloromethane. The combined organic fractions were washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 8.6 g of 5-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionthe mixture was then extracted with dichloromethane
  3. washThe combined organic fractions were washed sequentially with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b09ed56d11514c39bd198994b727f15a
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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