Hydrochloric Acid → HCID 131721182, compound

HRID 1418315Notes

Reaction equation

HRID 1418315 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][OH:5].[F:10][C:11]1[CH:16]=[C:15](F)[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]=1[N:21]1[C:29](=[O:30])[C:24]2=[CH:25][CH2:26][CH2:27][CH2:28][N:23]2[C:22]1=[O:31].Cl>C(OCC)(=O)C.O1CCOCC1>[CH2:8]([O:7][C:3]([CH2:4][O:5][C:15]1[C:14]([N+:18]([O-:20])=[O:19])=[CH:13][C:12]([N:21]2[C:29](=[O:30])[C:24]3=[CH:25][CH2:26][CH2:27][CH2:28][N:23]3[C:22]2=[O:31])=[C:11]([F:10])[CH:16]=1)=[O:6])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 131721183HCID 131721183, compound

Product 1

HCID 131721182HCID 131721182, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium hydride (0.06 g, 2.4 mmol) was put in to a flask, to which 1,4-dioxane (5 mL) and ethyl glycolate (0.12 mL, 1.32 mmol) was added with stirring under cooling in an ice-water bath after replacing the inside of flask throughly with argon gas, and the mixture was stirred for 15 minutes at the ambient temperature. Then, 2-(2,4-difluoro-5-nitrophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.37 g, 1. mmol) was added to the mixture at the same temperature. The reaction mixture was wormed up to room temperature and stirred for 3 hours, and further stirred for 13 hours at 80° C. 1N Hydrochloric acid (10 mL) and ethyl acetate (10 mL) were added to the resulting mixture and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (10 mL ×2 times). The organic layer combined was washed with a saturated sodium bicarbonate (20 mL) and a saturated sodium chloride solution (20 mL), and dried over anhydrous magnesium sulfate. After removal of magnesium sulfate by filtration, the filtrate was evaporated to give crude product, which was purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/2) to obtain a white solid of 2-(4-ethoxycarbonylmethoxy-2-fluoro-5-nitrophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.23 g, yield:48.9%).

Workup

  1. additionwas added
  2. temperatureunder cooling in an ice-water bath
  3. stirringthe mixture was stirred for 15 minutes at the ambient temperature
  4. customwas wormed up to room temperature
  5. stirringstirred for 3 hours
  6. stirringfurther stirred for 13 hours at 80° C
  7. customthe organic layer was separated
  8. extractionThe aqueous layer was extracted with ethyl acetate (10 mL ×2 times)
  9. washThe organic layer combined was washed with a saturated sodium bicarbonate (20 mL)
  10. dry with materiala saturated sodium chloride solution (20 mL), and dried over anhydrous magnesium sulfate
  11. customAfter removal of magnesium sulfate
  12. filtrationby filtration
  13. customthe filtrate was evaporated
  14. customto give crude product, which
  15. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-836509e3d47c41b989b4e83b83839e68
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

Loading…