Hydrochloric Acid → HCID 15390589, compound

HRID 1418292Notes

Reaction equation

HRID 1418292 reaction equation
CO.[Cl:3][C:4]1[C:9]([O:10]C(OC)=O)=[CH:8][C:7]([N:15]2[C:23](=[O:24])[C:18]3=[CH:19][CH2:20][CH2:21][CH2:22][N:17]3[C:16]2=[O:25])=[C:6]([F:26])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(OCC)C>[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][C:7]([N:15]2[C:23](=[O:24])[C:18]3=[CH:19][CH2:20][CH2:21][CH2:22][N:17]3[C:16]2=[O:25])=[C:6]([F:26])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 131721157HCID 131721157, compound

Product 1

HCID 15390589HCID 15390589, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A methanol (40 mL) solution of 2-(4-chloro-2-fluoro-5-methoxycarbonyloxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (3.13 g, 8.8 mmol) and potassium carbonate (1.22 g, 8.8 mmol) was stirred at 50°-60° C. for 8 hours. Diethyl ether (20 mL) and 1N hydrochloric acid (30 mL) were added to the resulting mixture, and the organic layer was separated and then the aqueous layer was extracted with diethyl ether (20 mL×2 times). The organic layer combined was washed with a saturated sodium chloride solution (30 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=1/1) to obtain a white solid of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.93 g, yield:5.8%).

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with diethyl ether (20 mL×2 times)
  3. washThe organic layer combined was washed with a saturated sodium chloride solution (30 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removal of magnesium sulfate
  6. filtrationby filtration
  7. customthe filtrate was evaporated
  8. customto give crude product, which
  9. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-5d4212cfbe8c443d94e8a2ca2efda4e9
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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