HCID 178485134, compound → HCID 178485132, compound

HRID 1067825Notes

Reaction equation

HRID 1067825 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]([N:24]=[C:25]([NH2:28])[NH:26][CH3:27])=[O:23])=[CH:18]2)=O)(C)(C)C>Cl.CO>[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:22]([N:24]=[C:25]([NH2:28])[NH:26][CH3:27])=[O:23])=[CH:18]2

Participants

3

Reactant 1

HCID 178485134HCID 178485134, compound

Product 1

HCID 178485132HCID 178485132, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

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

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionAfter 2N sodium hydroxide aqueous solution was added to the residue
  3. customthus obtained
  4. extractionthe mixture was extracted three times with chloroform
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customThe resulting residue was isolated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-d521299ac7d24f5c953e8433ee59d7ac
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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