Hydrochloric Acid → (S)-1-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propylamine

HRID 1698226Notes

Reaction equation

HRID 1698226 reaction equation
[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C@@H:15]([NH:18]S(C(C)(C)C)=O)[CH2:16][CH3:17])=[N:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.Cl.O1CCOCC1>CO>[C:1]1([CH3:25])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C@@H:15]([NH2:18])[CH2:16][CH3:17])=[N:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 667275192-methyl-propane-2-sulfinic acid {(S)-1-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propyl}-amide

Product 1

HCID 59278418(S)-1-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid {(S)-1-[1-(toluene-4-sulfonyl)-1H-pyrazol-3-yl]-propyl}-amide (1.00 g, 2.61 mmol) in MeOH was added a 4 M solution of HCl in dioxane (1 mL, 4 mmol). After 2 hours, the solvent was concentrated in vacuo. The residue was made basic with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound.

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b69c8a6d4f184e41a15b284c6e6a39f4
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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