Ethoxyacetyl chloride → HCID 21936599, compound

HRID 1350028Notes

Reaction equation

HRID 1350028 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:26]([O:28][CH2:29][C:30](Cl)=O)[CH3:27]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:26]([O:28][CH2:29][C:30]1[N:12]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:27]

Participants

5

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 12106200Tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy)ethylcarbamate

Product 1

HCID 21936599HCID 21936599, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (18.04 g, 52.1 mmol) in 180 mL of pyridine was treated with 50 mg of 4-dimethylaminopyridine and chilled in an ice water bath. 2-ethoxyacetyl chloride (6.44 g, 52.6 mmol) was added dropwise to the solution. The reaction was stirred at room temperature for 3 h. The reaction was then heated to reflux with stirring. After 18 h the reaction was cooled and then concentrated. The residue was partitioned between CHCl3 (150 mL) and water (150 mL) and the layers were separated. The aqueous portion was extracted with CHCl3 (3×50 mL). The combined organic portions were washed with brine, dried over Na2SO4, filtered and concentrated to yield 15.47 g of tert-butyl 2-{2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate as a sticky yellow solid.

Workup

  1. temperaturechilled in an ice water bath
  2. temperatureThe reaction was then heated
  3. temperatureto reflux
  4. stirringwith stirring
  5. temperatureAfter 18 h the reaction was cooled
  6. concentrationconcentrated
  7. customThe residue was partitioned between CHCl3 (150 mL) and water (150 mL)
  8. customthe layers were separated
  9. extractionThe aqueous portion was extracted with CHCl3 (3×50 mL)
  10. washThe combined organic portions were washed with brine
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-13a74e400e364c699c2b92a935592ec0
Source dataset
uspto-grants-2007_05
Patent number
US07214675B2

Reaction notes

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