Hydrochloric Acid → HCID 178485133, compound

HRID 1067826Notes

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-fc027cb29be04fc1ae7ed6f5cac7fce0
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248772B1

Reaction notes

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