HCID 23369714, compound → HCID 23369801, compound

HRID 1900823Notes

Reaction equation

HRID 1900823 reaction equation
[N:1]([CH:4]([CH:6]1[O:21][C:9]2=[C:10]3[C:15](=[C:16]([CH3:18])[CH:17]=[C:8]2[CH:7]1[CH3:22])[NH:14][C:13](=[O:19])[C:12]([CH3:20])=[CH:11]3)[CH3:5])=[N+]=[N-].[H][H]>CO.O1CCCC1.CN(C)C=O.[Pd]>[NH2:1][CH:4]([CH:6]1[O:21][C:9]2=[C:10]3[C:15](=[C:16]([CH3:18])[CH:17]=[C:8]2[CH:7]1[CH3:22])[NH:14][C:13](=[O:19])[C:12]([CH3:20])=[CH:11]3)[CH3:5]

Participants

7

Reactant 2

HCID 23369714HCID 23369714, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23369801HCID 23369801, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 290 (2.08 g, 7.0 mmol) was dissolved in a mixture of methanol (30 ml), tetrahydrofuran (30 ml) and dimethylformamide (30 ml). To the obtained solution, 10% palladium-on-carbon (0.70 g) was added, and allowed to react at ambient temperature for 4 hours in the stream of hydrogen gas. The insoluble matter was removed by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (benzene:methanol=2:1) to obtain 1.25 g of the title compound as a colorless solid (66.0%, mp.: 195°-207° C.)

Workup

  1. customThe insoluble matter was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (benzene:methanol=2:1)

Sources & evidence

ORD record
ord-2411f73fa7bf4d94ae65f5cb7b9f6377
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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