HCID 19434860, compound → HCID 19434930, compound

HRID 1736154Notes

Reaction equation

HRID 1736154 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]2[O:16][C:17]3[C:25]([F:26])=[C:24]([CH3:27])[C:23]([F:28])=[C:22]([NH:29]C(=O)C(C)(C)C)[C:18]=3[C:19](=[O:21])[CH:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8]C(=O)C(C)(C)C>S(=O)(=O)(O)O>[NH2:29][C:22]1[C:18]2[C:19](=[O:21])[CH:20]=[C:15]([C:4]3[CH:5]=[CH:6][C:7]([NH2:8])=[C:2]([Cl:1])[CH:3]=3)[O:16][C:17]=2[C:25]([F:26])=[C:24]([CH3:27])[C:23]=1[F:28]

Participants

3

Reactant 1

HCID 19434860HCID 19434860, compound

Product 1

HCID 19434930HCID 19434930, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

8.29 g (16.5 mmol) of the above 2-(3-chloro-4-pivaloylaminophenyl)-6,8-difluoro-7-methyl-5-pivaloylamino-4H-1-benzopyran-4-one was dissolved in 60 mL of concentrated sulfuric acid and the solution was stirred at 50° C. for 10 minutes. The reaction solution was poured into ice water and the precipitated crystals were collected by filtration. The crystals were triturated with a 1N aqueous solution of sodium hydroxide and collected by filtration again. The crystals were recrystallized twice from ethyl acetate/n-hexane to give 2.42 g of Compound 103 (yield: 44%).

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customThe crystals were triturated with a 1N aqueous solution of sodium hydroxide
  3. filtrationcollected by filtration again
  4. customThe crystals were recrystallized twice from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-68a9bffd534d4017b8d07584a7740c59
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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