Triethylamine → HCID 68974210, compound

HRID 2383212Notes

Reaction equation

HRID 2383212 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[NH2:31])([CH3:4])([CH3:3])[CH3:2].[CH2:33]([O:35][CH2:36][C:37](Cl)=O)[CH3:34].C(N(CC)CC)C>ClCCl.C(O)C>[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:13]2[C:22]3[CH:21]=[CH:20][C:19]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:31]=[C:34]1[CH2:33][O:35][CH2:36][CH3:37])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 68900070Tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamate

Product 1

HCID 68974210HCID 68974210, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl{4-[3-amino-7-(benzyloxy)quinolin-4-ylamino]butyl}carbamate (28.1 g, 64.3 mmol) was dissolved in dichloromethane (319 mL). Ethoxyacetyl chloride (7.87 g, 64.5 mmol) was added dropwise via an addition funnel and the mixture was stirred for 1 hour. The dichloromethane was removed under reduced pressure and the resulting residue was dissolved in a solution of triethylamine (35.84 mL, 0.26 mol) and ethanol (319 mL). The reaction was heated at reflux for 4 hours, and then allowed to cool overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane. The organic fraction was washed sequentially with water and saturated aqueous sodium chloride; dried over anhydrous sodium sulfate; filtered; and concentrated under reduced pressure. The oily residue was dissolved in acetonitrile. The acetonitrile was subsequently removed under reduced pressure to provide 30 g of tert-butyl[4-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate as a brown solid.

Workup

  1. customThe dichloromethane was removed under reduced pressure
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 4 hours
  4. temperatureto cool overnight
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in dichloromethane
  7. washThe organic fraction was washed sequentially with water and saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationand concentrated under reduced pressure
  11. dissolutionThe oily residue was dissolved in acetonitrile
  12. customThe acetonitrile was subsequently removed under reduced pressure

Sources & evidence

ORD record
ord-11f0616fa83541389f7d8a13c4c54f04
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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