Diethylamine → HCID 178464070, compound

HRID 2239992Notes

Reaction equation

HRID 2239992 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.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>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:35]([CH2:36][CH3:37])[CH2:33][CH3:34])[CH:17]=3)[NH:12][N:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8021Diethylamine2×HCID 178427774HCID 178427774, compound

Product 1

HCID 178464070HCID 178464070, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of toluene-4-sulfonic acid 2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl ester (0.420 g, 0.889 mmol) and diethylamine (1.0 mL, 9.7 mmol) in THF (8 mL) was stirred at 70° C. for 6 hours in a sealed tube. Additional diethylamine (1.0 mL, 9.7 mmol) was added, and the reaction mixture was stirred at 80° C. in a sealed tube for an 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 in vacuo at 80° C. for 20 minutes, [2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl]-diethyl-amine as a pale yellow solid (0.155 g, 46.6%) was obtained. This was dissolved in methanol and chloroform and ethereal hydrochloride was added. The mixture was concentrated and dried in vacuo at 74° C. for 13.5 hours to yield the hydrochloride as a light orange foam (0.163 g); Mass Spectrum (+EI, [M+H]+) m/z 374. 1HNMR (500 MHz, DMSO-d6): δ14.24 (s, 1H), 9.94 (br, 1H), 7.96-7.99 (m, 2H), 7.56-7.68 (m, 4H), 7.41 (d, 1H, J=2.20 Hz), 7.16-7.19 (m, 1H), 4.40-4.43 (m, 2H), 3.52 (br, 2H), 3.19-3.23 (m, 4H), 1.23 ppm (t, 6H, J=7.20 Hz). Elemental Analysis for C19H23N3O3S.1.00 mol HCl.0.20 mol H2O: Calcd: C, 55.18; H, 5.95; N, 10.16; Found: C, 54.85; H, 5.85; N, 10.02.

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 80° C. for 20 minutes

Sources & evidence

ORD record
ord-ca8e4697cf4b46d5a721fa09bf65db8d
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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