Hydrochloric Acid → 4-Guanidinoimino-1-methanesulfonyl-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindole hydrochloride

HRID 1700539Notes

Reaction equation

HRID 1700539 reaction equation
[CH3:1][S:2]([N:5]1[C:13]2[CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[CH2:10][C:9](=O)[C:8]=2[C:7]([CH3:22])=[CH:6]1)(=[O:4])=[O:3].[C:23]([NH:26][NH2:27])([NH2:25])=[NH:24].[ClH:28].Cl.O>C(O)C>[ClH:28].[NH:26]([N:27]=[C:9]1[CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:12][C:13]2[N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=[C:7]([CH3:22])[C:8]1=2)[C:23]([NH2:25])=[NH:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18317793HCID 18317793, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 1784241714-Guanidinoimino-1-methanesulfonyl-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindole hydrochlorideYield 61.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-methanesulfonyl-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindol-4-one (0.20 g), aminoguanidine hydrochloride (0.073 g), concentrated hydrochloric acid (0.032 ml), water (0.032 ml) and ethanol (20 ml) was refluxed for 30 minutes. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the organic layer was purified with silica gel column chromatography (EtOAc/MeOH). To the resulting crystals was added 1N hydrochloric acid, and the mixture was concentrated. The residue was recrystallized from ethanol-ethyl acetate to give 4-guanidinoimino-1-methanesulfonyl-3-methyl-6-(2-methylphenyl)-4,5,6,7-tetrahydroindole hydrochloride (Compound 15) (0.16 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionto the residue was added sodium hydrogen carbonate solution
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe organic layer was purified with silica gel column chromatography (EtOAc/MeOH)
  6. additionTo the resulting crystals was added 1N hydrochloric acid
  7. concentrationthe mixture was concentrated
  8. customThe residue was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-dfc8055cf8d74145a3715a3c941ce925
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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