Hydrochloric Acid → HCID 15840027, compound

HRID 745004Notes

Reaction equation

HRID 745004 reaction equation
[NH2:1][S:2]([CH:5]=[CH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][C@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[CH3:22])(=[O:4])=[O:3].Cl>C(O)C.[Pd]>[NH2:1][S:2]([CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][C@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[CH3:22])(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54324308HCID 54324308, compound

Product 1

HCID 15840027HCID 15840027, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-5-(2-Aminosulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole (157 mg, 0.5 mmol) was dissolved in absolute ethanol (10 mL) and added to a solution of ethanolic hydrogen chloride (25 ml) (prepared from acetyl chloride (38 μL, 0.53 mmol) and absolute ethanol (25 mL)). 10% palladium-on-carbon (125 mg) was added. This solution was hydrogenated under a hydrogen atmosphere (15 p.s.i.) at room temperature for 18 hours. The resultant reaction mixture was filtered through diatomaceous earth (Celite trademark or Arbacell-trademark)) washed with absolute ethanol and the combined filtrates evaporated in vacuo. The residue was purified by column chromatography on silica gel, eluting with a gradient solvent mixture up to CH2Cl2 : MeOH:NH4OH 93:7:1 to give the title compound as a colourless oil (80 mg, 51%). Anal. Calcd for C16H23N3O2S·1/4 MeOH. 1/3 H2O: C,58.21; H,7.36; N,12.54. Found: C,58.60; H,7.40; N,12.57. [α]25 D =+69° (c=0.1, MeOH).

Workup

  1. customat room temperature
  2. customfor 18 hours
  3. customThe resultant reaction mixture
  4. filtrationwas filtered through diatomaceous earth (Celite trademark or Arbacell-trademark))
  5. washwashed with absolute ethanol
  6. customthe combined filtrates evaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with a gradient solvent mixture up to CH2Cl2 : MeOH:NH4OH 93:7:1

Sources & evidence

ORD record
ord-6410a8a7bee14f3b8bd14d4a032b4c69
Source dataset
uspto-grants-1996_09
Patent number
US05559246

Reaction notes

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