HCID 20083185, compound → HCID 21733326, compound

HRID 1609103Notes

Reaction equation

HRID 1609103 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]([NH:13]CC2C=CC=CC=2)[C:9]2[C:21](=[O:29])[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:23][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH3:30]>C(O)C.C(O)(=O)C.[Pd]>[F:1][C:2]1[C:11]([F:12])=[C:10]([NH2:13])[C:9]2[C:21](=[O:29])[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:23][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH3:30]

Participants

5

Reactant 1

HCID 20083185HCID 20083185, compound

Product 1

HCID 21733326HCID 21733326, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

59 mg of the compound (200) obtained in Example 71 was dissolved in 10 ml of ethanol and 10 ml of acetic acid, and 5 mg of 10% palladium on carbon was added to the solution. the solution was stirred for 24 hours under hydrogen. The catalyst was filtered, and the filtrate was evaporated. The residue was dissolved in chloroform and was washed with saturated aqueous sodium hydrogen-carbonate solution. After drying over magnesium sulfate, the solvent was removed by distillation. Solids were dispersed in ether and filtered off to obtain 27 mg of the subject compound (201) in a 59% yield.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in chloroform
  4. washwas washed with saturated aqueous sodium hydrogen-carbonate solution
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solvent was removed by distillation
  7. additionSolids were dispersed in ether
  8. filtrationfiltered off

Sources & evidence

ORD record
ord-a6389e5e4e5446b2ad0a19d7b22eeca2
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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