HCID 23369851, compound → HCID 23369782, compound

HRID 1900790Notes

Reaction equation

HRID 1900790 reaction equation
[N:1]([CH2:4][CH:5]1[O:21][C:8]2=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:18])[C:11]([CH3:19])=[C:10]3[CH3:20])=[N+]=[N-].[H][H]>O1CCCC1.CO.[Pd]>[NH2:1][CH2:4][CH:5]1[O:21][C:8]2=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:18])[C:11]([CH3:19])=[C:10]3[CH3:20]

Participants

6

Reactant 2

HCID 23369851HCID 23369851, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23369782HCID 23369782, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 255 (1.05 g, 3.69 mmol) was dissolved in a solvent mixture of tetrahydrofuran (50 ml) and methanol (20 ml). To the solution, 10% palladium-on-carbon (1 g) was added, followed by stirring at 50° C. for 4 hours in the atmosphere of hydrogen. The catalyst was removed by filtration, and the catalyst was evaporated under reduced pressure. As a result, 658 mg of the title compound was obtained as colorless powder (69.1%). The obtained powder was dissolved in methanol (20 ml), to which 4N-HCl in 1,4-dioxane (0.7 ml) was added. Recrystallization from chloroform--methanol--ether yielded 536 mg of the title compound as pale yellow powder (49.3%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe catalyst was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9b534fa766c74814ab5df7923101d6e4
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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