Hydrochloric Acid → HCID 178485133, compound

HRID 565039Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([N:17]=[C:18]([NH2:21])[NH:19][CH3:20])=[O:16])=[CH:11]2.[ClH:22].Cl.CO>>[ClH:22].[ClH:22].[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([N:17]=[C:18]([NH2:21])[NH:19][CH3:20])=[O:16])=[CH:11]2

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 21893726Hydrochloride methanol

HCID 178485132HCID 178485132, compound

Product 1

HCID 178485133HCID 178485133, compound

Procedure

After 0.04 g (0.10 mmol) of 7-[(3-tert-butoxycarbonylaminopropyl)amino]-1-methyl-2-indoloylguanidine was dissolved in 2 ml of hydrochloric acid/methanol, the solution was stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure. After 2N sodium hydroxide aqueous solution was added to the residue thus obtained, the mixture was extracted three times with chloroform. The combined extracts were dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was isolated and purified by silica gel column chromatography to give 0.023 g (80.0%) of 7-[(3-aminopropyl)amino]-1-methyl-2-indoloylguanidine. The guanidine derivative was converted into the hydrochloride with hydrochloric acid/methanol. Recrystallization from methanol gave 7-[(3-aminopropyl)amino]-1-methyl-2-indoloylguanidine dihydrochloride.

Workup

customRecrystallization from methanol

Sources & evidence

ORD record: ord-f73d5d62967d4dd29807469dbe9a5f76
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169107A

Reaction notes

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