Hydrochloride methanol → HCID 178485157, compound

HRID 565017Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]=[C:14]([NH2:17])[NH:15][CH3:16])=[O:12])=[CH:5]2.[ClH:18].CO>>[ClH:18].[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]=[C:14]([NH2:17])[NH:15][CH3:16])=[O:12])=[CH:5]2

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 178485156HCID 178485156, compound

Product 1

HCID 178485157HCID 178485157, compoundYield 68.6%

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.

Sources & evidence

ORD record: ord-59a824c7b753448b848074f3aa82f926
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169107A

Reaction notes

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