Isopropylamine → HCID 178457411, compound

HRID 2239993Notes

Reaction equation

HRID 2239993 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.[CH:33]([NH2:36])([CH3:35])[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][NH:36][CH:33]([CH3:35])[CH3:34])[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 6363Isopropylamine2×HCID 178427774HCID 178427774, compound

Product 1

HCID 178457411HCID 178457411, compound

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 (0.378 g, 0.800 mmol) and isopropylamine (1.0 mL, 12 mmol) in THF (8 mL) was stirred at 70° C. for 6 hours in a sealed tube. Additional isopropyl amine (1.0 mL, 12 mmol) was added, and the reaction mixture was stirred at 80° 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 80° C. for 30 minutes, [2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl]-isopropyl-amine as a pale yellow solid was obtained (0.110 g, 38.2%). 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 an off-white solid (0.117 g): MP: 275-7° C. (dec); Mass Spectrum (+EI, [M+H]+) m/z 360. 1HNMR (500 MHz, DMSO-d6): δ14.22 (br, 1H), 8.75 (br, 2H), 7.96-7.98 (m, 2H), 7.56-7.68 (m, 4H), 7.41 (d, 1H, J=2.08 Hz), 7.19 (dd, 1H, J=9.15 Hz and 2.32 Hz), 4.30-4.33 (m, 2H), 3.34-3.40 (m, 3H), 1.25 ppm (d, 6H, J=6.59 Hz). Elemental Analysis for C18H21N3O3S.1.00 mol HCl.0.10 mol H2O: Calcd: C, 54.36; H, 5.36; N, 10.57; Found: C, 54.02; H, 5.42; N, 10.22.

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 30 minutes

Sources & evidence

ORD record
ord-deccbecceed649269996f95f2d78a5d7
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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