Butylamine → HCID 178449100, compound

HRID 2239994Notes

Reaction equation

HRID 2239994 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]([NH2:37])[CH2:34][CH2:35][CH3:36]>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][NH:37][CH2:33][CH2:34][CH2:35][CH3:36])[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 2

HCID 8007ButylamineHCID 178427774HCID 178427774, compound

Product 1

HCID 178449100HCID 178449100, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of toluene-4-sulfonic acid 2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl ester (0.348 g, 0.736 mmol) and n-butylamine (1.0 mL, 10 mmol) in THF (8 mL) 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 7.5-10% methanol in chloroform. After drying in vacuo at 55° C. for 40 minutes, [2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl]-butyl-amine as a light beige semi-solid (0.105 g, 38.2%) was obtained. This was dissolved in chloroform, and ethereal hydrochloride was added. The resulting solid was filtered and dried in vacuo at 75° C. for 16.5 hours to yield the hydrochloride as a white solid (0.0813 g): MP: 271-3° C. dec; Mass Spectrum (+EI, [M+H]+) m/z 374. 1HNMR (300 MHz, DMSO-d6): δ14.27-14.35 (br, 1H), 8.98-9.00 (br, 2H), 8.03-8.06 (m, 2H), 7.62-7.76 (m, 4H), 7.46 (d, 1H, J=2.19 Hz) 7.25 (dd, 1H, J=9.15 Hz and 2.29 Hz), 4.38-4.41 (m, 2H), 3.41-3.44 (m, 2H), 3.03 (t, 2H, J=7.87 Hz), 1.62-1.72 (m, 2H), 1.33-1.45 (m, 2H), 0.94 ppm (t, 3H, J=7.32 Hz). Elemental Analysis for C19H23N3O3S.1.00 mol HCl.0.05 mol H2O: Calcd: C, 55.55; H, 5.91; N, 10.23; Found: C, 55.23; H, 5.87; N, 10.09.

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 55° C. for 40 minutes

Sources & evidence

ORD record
ord-3e353fba034d4ce6a4b11340042fbc1b
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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