Hydrochloric Acid → HCID 131721181, compound

HRID 1418314Notes

Reaction equation

HRID 1418314 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[C:9]([Cl:26])=[CH:10][C:11]([F:25])=[C:12]([N:14]2[C:22](=[O:23])[C:17]3=[CH:18][CH2:19][CH2:20][CH2:21][N:16]3[C:15]2=[O:24])[CH:13]=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.Cl>C(OCC)(=O)C>[Cl:26][C:9]1[C:8]([NH:7][S:33]([C:30]2[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=2)(=[O:35])=[O:34])=[CH:13][C:12]([N:14]2[C:22](=[O:23])[C:17]3=[CH:18][CH2:19][CH2:20][CH2:21][N:16]3[C:15]2=[O:24])=[C:11]([F:25])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 131721162HCID 131721162, compound

Product 1

HCID 131721181HCID 131721181, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a pyridine (5 mL) solution of 2-(5-amino-4-chloro-2-fluorophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1, 3[2H, 7H]-dione (0.35 g, 1.2 mmol) was dropwise added p-toluenesulfonyl chloride (0.25 g, 1.3 mmol) under cooling in an ice-water bath, and the mixture was stirred for 2.5 hours at the ambient temperature. 1N Hydrochloric acid (60 mL) and ethyl acetate (40 mL) were added to the resulting mixture and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (20 mL×2 times), and the organic layer combined was washed with a saturated sodium chloride solution (100 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-chloro-2-fluoro-5-(p-toluenesulfonylamino)phenyl]-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.32 g, yield:59.3%).

Workup

  1. temperatureunder cooling in an ice-water bath
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (20 mL×2 times)
  4. washthe organic layer combined was washed with a saturated sodium chloride solution (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of magnesium sulfate
  7. filtrationby filtration
  8. customthe filtrate was evaporated
  9. customto give crude product, which
  10. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane =1/2)

Sources & evidence

ORD record
ord-745849f0c418483a868d74f9b376b28b
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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