Ethylamine → HCID 178464421, compound

HRID 2239991Notes

Reaction equation

HRID 2239991 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.[CH2:38]([NH2:40])[CH3:39]>>[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][NH:40][CH2:38][CH3:39])[CH:17]=3)[NH:12][N:11]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 178427774HCID 178427774, compound

Product 1

HCID 178464421HCID 178464421, compoundYield 43.9%

Procedure

A solution of toluene-4-sulfonic acid 2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl ester (0.361 g, 0.764 mmol) in 2.0 N ethylamine in THF (9 mL, 18 mmol) 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 then washed with water and brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 10% methanol in chloroform. After drying in vacuo at 68° C. for 20 minutes, [2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl]-ethyl-amine as a light brown gum (0.116 g, 43.9%) was obtained. This was dissolved in chloroform and methanol, and ethereal hydrochloride was added. Concentrating and drying at 74° C. for 13.5 hours in vacuo yielded the hydrochloride as a buff solid (0.113 g): MP: 248-50° C. (dec). Mass Spectrum (+EI, [M+H]+) m/z 346. 1HNMR (500 MHz, DMSO-d6): δ14.23 (s, 1H), 8.81 (br, 2H), 7.96-7.98 (m, 2H), 7.56-7.68 (m, 4H), 7.40 (d, 1H, J=2.07 Hz), 7.19 (dd, 1H, J=9.15 Hz and 2.32 Hz), 4.31 (t, 2H, J=5.00 Hz), 3.35 (br, 2H), 3.00-3.05 (m, 2H), 1.18-1.22 ppm (m, 3H).

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 in vacuo at 68° C. for 20 minutes

Sources & evidence

ORD record
ord-3b9da54cbc564203823f53e86a69bdcf
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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