Dimethylamine → [2-(3-Benzenesulfonyl-1H-indazol-5-yloxy)-ethyl]-dimethyl-amine

HRID 2239990Notes

Reaction equation

HRID 2239990 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.C1COCC1.[CH3:38][NH:39][CH3:40]>>[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:39]([CH3:40])[CH3:38])[CH:17]=3)[NH:12][N:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 178427774HCID 178427774, compound

Product 1

HCID 178483861[2-(3-Benzenesulfonyl-1H-indazol-5-yloxy)-ethyl]-dimethyl-amineYield 67.1%

Procedure

A solution of toluene-4-sulfonic acid 2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl ester (0.341 g, 0.722 mmol) in 2.0 N dimethylamine in THF (9 mL, 18 mmol) of was stirred at 70° C. for 6 hours in a sealed tube. After cooling somewhat, the reaction mixture was solvent evaporated and partitioned in ethyl acetate and aqueous sodium bicarbonate. The organic phase was washed with water and brine. It was dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was partitioned in ethyl acetate/aqueous potassium carbonate. The organic phase was washed with water and brine, dried with anhydrous magnesium sulfate, filtered and concentrated. [2-(3-Benzenesulfonyl-1H-indazol-5-yloxy)-ethyl]-dimethyl-amine as a light yellow-brown solid (0.167 g, 67.1%) resulted. The compound was dissolved in methanol, and ethereal hydrochloride was added. After concentrating and drying in vacuo for 12 hours at 70° C., the hydrochloride as a light orange foam (94.0 mg) was obtained; Mass Spectrum (+EI, [M+H]+) m/z 346. 1HNMR (500 MHz, DMSO-d6): δ14.22 (s, 1H), 10.00 (br, 1H), 7.97-7.99 (m, 2H), 7.56-7.68 (m, 4H), 7.42 (d, 1H, J=2.20 Hz), 7.17-7.20 (m, 1H), 4.39-4.42 (m, 2H), 3.52-3.53 (m, 2H), 2.84 ppm (s, 6H).

Workup

  1. temperatureAfter cooling somewhat
  2. customevaporated
  3. custompartitioned in ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialIt was dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was partitioned in ethyl acetate/aqueous potassium carbonate
  9. washThe organic phase was washed with water and brine
  10. dry with materialdried with anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-664507aeb73e49aca5bbe4abd0d54c1b
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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