Methanol → 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinoline

HRID 540841Notes

Reaction equation

HRID 540841 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([OH:15])=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:16]=1)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)=[O:30].CO>CN(C=O)C.O.C(OCC)C>[CH2:1]([C:3]1[N:4]([CH2:17][CH:18]([CH3:19])[CH3:20])[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([O:15][CH2:28][C:29]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[O:30])=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:16]=1)[CH3:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 139968762-Bromo-1-(morpholin-4-yl)ethan-1-oneHCID 1363478472-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol

Product 1

HCID 689692552-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinolineYield 94.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
85 °C

Procedure

Under a nitrogen atmosphere, a mixture of 2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (1.97 g, 7.31 mmol), solid cesium carbonate (4.77 g, 14.6 mmol), and DMF (105 mL) was heated at 85° C. for 30 minutes. The heat was removed, and a solution of 4-(2-bromoacetyl)morpholine (1.83 g, 8.77 mmol) in DMF (20 mL) was added over a period of 12 minutes. The reaction was heated at 85° C. for 3.5 hours, and methanol (1 mL) was then added. The reaction mixture was filtered to remove solids, and the filtrate was concentrated under reduced pressure to provide an orange oil. The oil was triturated with ethyl acetate and water to provide a fluffy, white solid that was isolated by filtration. The filtrate was concentrated under reduced pressure to provide a solid that was stirred with diethyl ether and water and isolated by filtration. The two solids were combined and dried in a vacuum oven at 60° C. to provide 2.75 g of 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinoline as a yellow semi-solid.

Workup

  1. customThe heat was removed
  2. temperatureThe reaction was heated at 85° C. for 3.5 hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove solids
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto provide an orange oil
  7. customThe oil was triturated with ethyl acetate and water
  8. customto provide a fluffy, white solid
  9. customthat was isolated by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customto provide a solid
  12. customisolated by filtration
  13. customdried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-bcea428d21f244f99603f5d41384e19f
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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