Triethylamine → N-(2-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}ethyl)morpholine-4-carboxamide hydrochloride

HRID 540818Notes

Reaction equation

HRID 540818 reaction equation
[N:1]1([C:7]([Cl:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:23]=[CH:22][C:21]2[N:20]=[C:19]([NH2:24])[C:18]3[N:25]=[C:26]([CH2:31][O:32][CH2:33][CH3:34])[N:27]([CH2:28][CH2:29][CH3:30])[C:17]=3[C:16]=2[CH:15]=1.C(N(CC)CC)C.[OH-].[Na+]>ClCCl>[ClH:9].[NH2:24][C:19]1[C:18]2[N:25]=[C:26]([CH2:31][O:32][CH2:33][CH3:34])[N:27]([CH2:28][CH2:29][CH3:30])[C:17]=2[C:16]2[CH:15]=[C:14]([O:13][CH2:12][CH2:11][NH:10][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[O:8])[CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 848104-Morpholinecarbonyl chlorideHCID 588336918-(2-aminoethoxy)-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 68973537N-(2-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}ethyl)morpholine-4-carboxamide hydrochlorideYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Morpholinecarbonyl chloride (0.177 mL, 1.52 mmol) was added dropwise to a solution of 8-(2-aminoethoxy)-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.500 g, 1.46 mmol) in dichloromethane, and the reaction was stirred for ten minutes. Triethylamine (0.418 mL, 3.00 mmol) was then added, and the reaction was stirred for 16 hours. Aqueous sodium hydroxide (50%) was added, and the mixture was stirred for 30 minutes and then diluted with dichloromethane (100 mL). The organic layer was separated, washed sequentially with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was then treated with concentrated hydrochloric acid and water. A precipitate formed and was isolated by filtration, washed with water and diethyl ether, and dried in a vacuum oven at 60° C. to provide 0.180 g of N-(2-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}ethyl)morpholine-4-carboxamide hydrochloride as a white solid, mp 200-202° C.

Workup

  1. stirringthe reaction was stirred for 16 hours
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe organic layer was separated
  4. washwashed sequentially with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was then treated with concentrated hydrochloric acid and water
  9. customA precipitate formed
  10. customwas isolated by filtration
  11. washwashed with water and diethyl ether
  12. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-ada5d0126ab34e9cbfdeed62899d3ec7
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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