Triethylamine → HCID 57447030, compound

HRID 2366620Notes

Reaction equation

HRID 2366620 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][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)CC)C.[CH2:30]([O:32][CH2:33][C:34](Cl)=O)[CH3:31]>C(Cl)(Cl)Cl>[CH2:30]([O:32][CH2:33][C:34]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[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)[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 57447017HCID 57447017, compound

Product 1

HCID 57447030HCID 57447030, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of ethyl 6-(3-aminoquinolin-4-ylamino)hexanoate (9.25 g, 30.7 mmol) in chloroform (100 mL) was cooled to 0° C.; triethylamine (5.13 mL, 36.8 mmol) was added. Ethoxyacetyl chloride (4.51 g, 36.8 mmol) was then added dropwise over a period of five minutes. The reaction was allowed to warm to ambient temperature, heated at reflux overnight, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 93:7 dichloromethane:methanol) to provide 7.73 g of ethyl 6-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoate.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel (eluting with 93:7 dichloromethane:methanol)

Sources & evidence

ORD record
ord-1c2120d34e084e129914bd58e24571df
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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