Triethylamine → HCID 86626177, compound

HRID 598371Notes

Reaction equation

HRID 598371 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][C:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:23])[CH3:22])=[CH:16][C:15]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[CH:14][CH:13]=2.C(N(CC)CC)C>ClCCl>[CH2:33]([O:32][C:15]1[CH:14]=[CH:13][C:12]2[N:11]=[CH:10][C:9]3[N:8]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:19]([CH2:20][C:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:23])[CH3:22])[C:18]=3[C:17]=2[CH:16]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 86626176HCID 86626176, compound

Product 1

HCID 86626177HCID 86626177, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethoxyacetyl chloride (3.5 mL, 32.0 mmol) was added to a solution of tert-butyl [2-(3-amino-6-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]carbamate (12.71 g, 29.1 mmol) and triethylamine (8.1 mL, 58.2 mmol) in approximately 250 mL of anhydrous dichloromethane. After stirring for 2 hours, the volatiles were removed under reduced pressure and the resulting brown residue was dissolved in ethanol, followed by the addition of 8.1 mL of triethylamine. The reaction was heated at reflux for 2.5 days and then cooled to ambient temperature. The solvent was removed under reduced pressure and dichloromethane was added. The solution was sequentially washed with aqueous sodium bicarbonate (2×) followed by brine; dried over sodium sulfate; filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on a HORIZON HPFC system. A silica gel cartridge was used eluting with a gradient of 0-15% CMA in chloroform to provide 8.4 g of tert-butyl [2-(8-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]carbamate as an orange foam.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionthe resulting brown residue was dissolved in ethanol
  3. additionfollowed by the addition of 8.1 mL of triethylamine
  4. temperatureThe reaction was heated
  5. temperatureat reflux for 2.5 days
  6. customThe solvent was removed under reduced pressure and dichloromethane
  7. additionwas added
  8. washThe solution was sequentially washed with aqueous sodium bicarbonate (2×)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by column chromatography on a HORIZON HPFC system
  13. washA silica gel cartridge was used eluting with a gradient of 0-15% CMA in chloroform

Sources & evidence

ORD record
ord-d5085a5a1b494d98a8e7a1a0fc79ea05
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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