HCID 178485155, compound → HCID 178485156, compound

HRID 565016Notes

Reaction equation

HRID 565016 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([N:20]=[C:21]([NH2:24])[NH:22][CH3:23])=[O:19])=[CH:12]2)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([N:20]=[C:21]([NH2:24])[NH:22][CH3:23])=[O:19])=[CH:12]2

Participants

4

Reactant 1

HCID 178485155HCID 178485155, compound

Product 1

HCID 178485156HCID 178485156, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In 50 ml of methanol was dissolved 0.83 g (2.58 mmol) of 5-benzyloxy-1-methyl-2-indoloylguanidine obtained in Example 32. While stirring at room temperature, 0.30 g of 10% palladium/carbon was added to the solution in a nitrogen flow and catalytic hydrogenation was then conducted at ambient temperature under normal pressure. After completion of the reaction, the catalyst was filtered off and the filtrate was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 5-hydroxy-1-methyl-2-indoloylguanidine. The 5-hydroxy-1-methyl-2-indoloylguanidine was further treated with hydrogen chloride/methanol to give 0.37 g (68.6%) of 5-hydroxy-1-methyl-2-indoloylguanidine hydrochloride.

Workup

  1. customwas then conducted at ambient temperature under normal pressure
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was then concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b52f7ca0563e4bb682c7ef44b4fde286
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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