Triethylamine → HCID 21936589, compound

HRID 432745Notes

Reaction equation

HRID 432745 reaction equation
[C:1]([NH:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:13][CH:12]=[CH:11][CH:10]=2)(=O)[CH2:2][CH3:3].C(N(CC)CC)C>CCO>[CH2:2]([C:1]1[N:16]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 21936609HCID 21936609, compound

Product 1

HCID 21936589HCID 21936589, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-(2-{[3-(propionylamino)quinolin-4-yl]amino}ethoxy)ethylcarbamate (15.00 g, 37.3 mmol) in 200 mL of EtOH was treated with triethylamine (13.0 mL, 93.2 mmol). The reaction was heated to reflux with stirring. After 3 days, the reaction was concentrated, triturated with ether and filtered to yield 13.78 g of tert-butyl 2-[2-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate as an off white solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. concentrationthe reaction was concentrated
  4. customtriturated with ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-8a30231e92c14a509ded7109c7582f4a
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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