Pyrrolidine → HCID 178527303, compound

HRID 2239997Notes

Reaction equation

HRID 2239997 reaction equation
[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:20][CH2:21]OS(C4C=CC(C)=CC=4)(=O)=O)[CH:17]=3)[NH:12][N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>C1COCC1>[C:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:20][CH2:21][N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)[CH:17]=3)[NH:12][N:11]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 178427774HCID 178427774, compound

Product 1

HCID 178527303HCID 178527303, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of toluene-4-sulfonic acid 2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl ester (0.347 g, 0.734 mmol) and pyrrolidine (1.0 mL, 12 mmol) in THF (8 mL) was stirred at 70° C. in a sealed tube for 6 hours. After cooling somewhat, the reaction mixture was solvent evaporated and partitioned in ethyl acetate and aqueous sodium bicarbonate. The organic phase was then washed with water and brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 7.5% methanol in chloroform. After drying at 55° C. in vacuo, 3-benzenesulfonyl-5-(2-pyrrolidin-1-yl-ethoxy)-1H-indazole as a pale yellow solid (0.0595 g, 21.8%) was obtained. This was dissolved in methanol and chloroform, and ethereal hydrochloride was added. The mixture was concentrated and dried in vacuo at 75° C. for 16.5 hours to yield the hydrochloride as a yellow foam (0.0598 g). Mass Spectrum (+EI, [M+H]+) m/z 372.

Workup

  1. temperatureAfter cooling somewhat
  2. customevaporated
  3. custompartitioned in ethyl acetate
  4. washThe organic phase was then washed with water and brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. customAfter drying at 55° C. in vacuo

Sources & evidence

ORD record
ord-9d7a7c9f8e9043fcbe8e921277e68709
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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