2-Pyrrolidone → HCID 67381991, compound

HRID 909340Notes

Reaction equation

HRID 909340 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:13]([CH2:22][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.N[C@@H]1CCCC[C@H]1N.[NH:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.O1CCOCC1>[CH2:24]([O:23][CH2:22][C:13]1[N:14]([CH2:15][CH2:16][CH2:17][O:18][CH:19]([CH3:21])[CH3:20])[C:6]2[C:5]3[CH:4]=[CH:3][C:2]([N:34]4[CH2:38][CH2:37][CH2:36][C:35]4=[O:39])=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:12]=1)[CH3:25]

Participants

7

Reactant 4

HCID 120252-PyrrolidoneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 67381991HCID 67381991, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline (0.5 g), copper(I) iodide (0.046 g), (+)-trans-1,2-diaminocyclohexane (0.030 mL), 2-pyrrolidinone (0.122 mL), potassium phosphate (0.55 g) and dioxane (1.2 mL) were added to a 2 dram vial with a stir bar. The vial was flushed with nitrogen, sealed with a Teflon-lined cap, placed in an oil bath, and heated at 110° C. for 16 hours. The reaction was cooled to ambient temperature and then diluted with chloroform and water. The layers were separated and the aqueous fraction was extracted with chloroform. The combined organic fractions were sequentially washed with water and saturated aqueous sodium chloride; dried over anhydrous sodium sulfate; filtered and concentrated under reduced pressure. The residue was purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument using a silica gel cartridge. The polar component of the eluent was chloroform:methanol:ammonium hydroxide 80:18:2 (CMA). The purification was carried out eluting with chloroform:CMA in a gradient from 99:1 to 80:20. 1-[2-Ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]pyrrolidin-2-one was isolated as a yellow oil which solidified over time (0.38 g).

Workup

  1. customThe vial was flushed with nitrogen
  2. customsealed with a Teflon-
  3. customlined cap
  4. customplaced in an oil bath
  5. temperatureThe reaction was cooled to ambient temperature
  6. additiondiluted with chloroform and water
  7. customThe layers were separated
  8. extractionthe aqueous fraction was extracted with chloroform
  9. washThe combined organic fractions were sequentially washed with water and saturated aqueous sodium chloride
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument
  14. customThe purification
  15. washwas carried out eluting with chloroform

Sources & evidence

ORD record
ord-d24e3b5e87824f5daed17585465bbc8e
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

Loading…