Sodium Bicarbonate → HCID 69506692, compound

HRID 2366677Notes

Reaction equation

HRID 2366677 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=O)[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:17]=1)[CH3:2].C([O-])(=O)C.[NH4+:30].C(=O)(O)[O-].[Na+]>O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21]([NH2:30])=[O:23])[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:17]=1)[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium Acetate2×HCID 57447013HCID 57447013, compound

Product 1

HCID 69506692HCID 69506692, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

Ethyl 4-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butanoate (15.9 g, 46.6 mmol, prepared as described in Parts A through C of Example 5) and ammonium acetate (35.0 g, 455 mmol) were sealed and heated in a high-pressure vessel at 130° C. for two days. An analysis by LC/NS indicated the presence of starting material, and additional ammonium acetate (15 g, 190 mmol) was added. The reaction was heated to 130° C. for several hours, allowed to cool to ambient temperature, stirred for three days, and poured into water (200 mL). Solid sodium bicarbonate was added until the solution was basic. The solution was extracted with dichloromethane (3×100 mL, 5×75 mL, and then in a continuous extractor for about 20 hours). The extracts were dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 10.3 g of 4-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butanamide as a light yellow solid.

Workup

  1. customwere sealed
  2. additionwas added
  3. temperatureThe reaction was heated to 130° C. for several hours
  4. temperatureto cool to ambient temperature
  5. extractionThe solution was extracted with dichloromethane (3×100 mL, 5×75 mL
  6. waitin a continuous extractor for about 20 hours)
  7. dry with materialThe extracts were dried over potassium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-890c0f70f2474548bacb8178147fdf6b
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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