Methanesulfonyl chloride → HCID 131721165, compound

HRID 1418300Notes

Reaction equation

HRID 1418300 reaction equation
[NH2:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([F:19])=[C:6]([N:8]2[C:16](=[O:17])[C:11]3=[CH:12][CH2:13][CH2:14][CH2:15][N:10]3[C:9]2=[O:18])[CH:7]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[Cl:20][C:3]1[C:2]([NH:1][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:7][C:6]([N:8]2[C:16](=[O:17])[C:11]3=[CH:12][CH2:13][CH2:14][CH2:15][N:10]3[C:9]2=[O:18])=[C:5]([F:19])[CH:4]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 131721162HCID 131721162, compound

Product 1

HCID 131721165HCID 131721165, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 (0.50 g, 1.69 mmol) was added methanesulfonyl chloride (0.14 mL, 1.86 mmol) with stirring under cooling in an ice-water bath and the reaction mixture was stirred for 2 hours at 0° C. The resulting mixture was quenched with 1N hydrochloric acid (60 mL) and extracted with ethyl acetate (20 mL×3 times). The organic layer combined was washed with 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=1/1) to obtain a white solid of 2-(4-chloro-2-fluoro-5-methanesulfonylaminophenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.46 g, yield:73.0%).

Workup

  1. temperatureunder cooling in an ice-water bath
  2. stirringthe reaction mixture was stirred for 2 hours at 0° C
  3. customThe resulting mixture was quenched with 1N hydrochloric acid (60 mL)
  4. extractionextracted with ethyl acetate (20 mL×3 times)
  5. washThe organic layer combined was washed with saturated sodium chloride solution (20 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removal of magnesium sulfate
  8. filtrationby filtration
  9. customthe filtrate was evaporated
  10. customto give crude product, which
  11. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-bf476846e9964b7aa70f31e4bc0a1e81
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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