Potassium Carbonate → tert-butyl 2-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate

HRID 606066Notes

Reaction equation

HRID 606066 reaction equation
[Cl:1][C:2]1[C:11]([NH:12][C:13](=O)[CH2:14][O:15][CH2:16][CH3:17])=[C:10]([NH:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(O)C.O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:14][O:15][CH2:16][CH3:17])[N:19]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:28])[CH3:26])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19096565Water ethanolHCID 86616883Tert-butyl 2-({2-chloro-3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)ethylcarbamate

Product 1

HCID 86616884tert-butyl 2-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamateYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the hydrochloride salt of tert-butyl 2-({2-chloro-3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)ethylcarbamate (2.50 g, 5.44 mmol) in 9:1 ethanol/water (50 mL) was added a solution of potassium carbonate (1.12 g, 8.16 mmol) in water (5 mL). The solution was heated to 50° C. for five hours. The solution was concentrated under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The aqueous layer was extracted with two additional portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to a pale yellow solid that was purified by flash chromatography (silica gel, gradient elution from 1:1 to 4:1 ethyl acetate/hexane) to afford the tert-butyl 2-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate as a white solid (1.55 g).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a pale yellow solid
  8. customthat was purified by flash chromatography (silica gel, gradient elution from 1:1 to 4:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a73e6fa97d734a05b5be0a872b0c677a
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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