HCID 23369803, compound → HCID 23369634, compound

HRID 1900743Notes

Reaction equation

HRID 1900743 reaction equation
[N:1]([CH2:4][CH:5]1[O:17][C:16]2[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:18])[CH2:10][CH2:9]3)[CH2:6]1)=[N+]=[N-].[H][H]>O1CCCC1.[C].[Pd]>[NH2:1][CH2:4][CH:5]1[O:17][C:16]2[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:18])[CH2:10][CH2:9]3)[CH2:6]1

Participants

5

Reactant 2

HCID 23369803HCID 23369803, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23369634HCID 23369634, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 161 (0.53 g, 2.17 mmol) dissolved in tetrahydrofuran (26 ml) was combined with 10% palladium-carbon (0.32 g), then stirred in the stream of hydrogen at ambient temperature for 1.5 hour. After completion of the reaction, palladium-carbon was filtered off from the reaction mixture. The palladium-carbon was washed with tetrahydrofuran and then methanol. The filtrate was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform: ammonia/methanol=20:1). 0.385 g of the tile compound was obtained as colorless crystals (87.9%, mp.: 162°-163° C.).

Workup

  1. filtrationwas filtered off from the reaction mixture
  2. washThe palladium-carbon was washed with tetrahydrofuran
  3. customcondensed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: chloroform: ammonia/methanol=20:1)

Sources & evidence

ORD record
ord-0c476bdceb9f4d4dafa546386555cdf3
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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