Triethylamine → HCID 59130427, compound

HRID 1992580Notes

Reaction equation

HRID 1992580 reaction equation
C([N:3](CC)CC)C.[NH2:8][O:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]([NH2:26])[C:16]=2[N:15]=[C:14]1[CH2:27][CH2:28][CH3:29].[CH:30]1([C:33](Cl)=[O:34])[CH2:32][CH2:31]1>C(Cl)(Cl)Cl>[OH-:9].[NH4+:3].[NH2:26][C:17]1[C:16]2[N:15]=[C:14]([CH2:27][CH2:28][CH3:29])[N:13]([CH2:12][CH2:11][CH2:10][O:9][NH:8][C:33]([CH:30]3[CH2:32][CH2:31]3)=[O:34])[C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 114494201H-Imidazo[4,5-c]quinolin-4-amine, 1-[3-(aminooxy)propyl]-2-propyl-

Product 2

HCID 14923Ammonium HydroxideHCID 59130427HCID 59130427, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Triethylamine (1.86 mL, 13.4 mmol) was added to a mixture of 1-[3-(aminooxy)propyl]-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 6.68 mmol), prepared as described in Example 1, and chloroform (20 mL). Cyclopropanecarbonyl chloride (673 microliters (μL), 7.35 mmol) was then added, and the resulting solution was stirred at room temperature overnight. The reaction was diluted with chloroform (50 mL), washed with brine (2×100 mL) and saturated aqueous sodium bicarbonate (2×100 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified twice by column chromatography on silica gel (eluting sequentially with 97:2:1-dichloromethane:methanol:ammonium hydroxide and 96:3:1-dichloromethane:methanol:ammonium hydroxide) to provide 532 milligrams (mg) of N-[3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propoxy]cyclopropanecarboxamide as a white powder, mp 103-105° C.

Workup

  1. customprepared
  2. washwashed with brine (2×100 mL) and saturated aqueous sodium bicarbonate (2×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified twice by column chromatography on silica gel (
  7. washeluting sequentially with 97:2

Sources & evidence

ORD record
ord-2a3e0658987c40bc9bde0964ed654332
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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