HCID 19434954, compound → HCID 19434886, compound

HRID 1736164Notes

Reaction equation

HRID 1736164 reaction equation
C([N:4]([C:11]1[C:35]([F:36])=[C:34]([NH:37]C(=O)C(C)(C)C)[C:14]2[C:15](=[O:33])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25]C(=O)C(C)(C)C)=[C:21]([F:32])[CH:20]=3)[O:18][C:13]=2[C:12]=1[F:44])[CH2:5][CH2:6][CH2:7][N:8]([CH3:10])[CH3:9])(=O)C>S(=O)(=O)(O)O>[NH2:37][C:34]1[C:14]2[C:15](=[O:33])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([F:32])[CH:20]=3)[O:18][C:13]=2[C:12]([F:44])=[C:11]([NH:4][CH2:5][CH2:6][CH2:7][N:8]([CH3:10])[CH3:9])[C:35]=1[F:36]

Participants

3

Reactant 1

HCID 19434954HCID 19434954, compound

Product 1

HCID 19434886HCID 19434886, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

549 mg (0.890 mmol) of the above 7-[N-acetyl-N-(3-dimethylaminopropyl)amino]-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pivaloylamino-4H-1-benzopyran-4-one was dissolved in 15 mL of concentrated sulfuric acid and the solution was stirred at 50° C. for 10 minutes. The reaction solution was poured into ice water, the mixture was adjusted to pH 8 and extracted once with ethyl acetate. The organic layer was washed once with water and once with an aqueous saturated solution of sodiumchloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=20:1:1) to give 297 mg of Compound 97 (yield: 82%). This compound was converted into hydrochloride according to the same manner as that in Example 96 (2).

Workup

  1. extractionextracted once with ethyl acetate
  2. washThe organic layer was washed once with water and once with an aqueous saturated solution of sodiumchloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=20:1:1)

Sources & evidence

ORD record
ord-c95d72e2ed8746c2a3d03f5cbfb7c836
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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