HCID 178514597, compound → HCID 178511386, compound

HRID 2240021Notes

Reaction equation

HRID 2240021 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[S:16]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[N+]=[N-]>C(O)C.[Pd]>[C:19]1([S:16]([C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([O:6][CH2:5][CH2:4][NH2:1])[CH:8]=3)[NH:12][N:11]=2)(=[O:17])=[O:18])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 178514597HCID 178514597, compound

Product 1

HCID 178511386HCID 178511386, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 5-(2-azido-ethoxy)-3-(naphthalene-1-sulfonyl)-1H-indazole (1.34 g, 3.41 mmol) in hot ethanol (210 mL) was added 10% palladium on carbon (0.8 g). The reaction mixture was hydrogenated on the Parr apparatus for 1.25 hours, starting pressure 49 psi. It was then filtered over Celite and concentrated. The residue was purified by flash chromatography with 0.5% ammonium hydroxide/5.0% methanol in chloroform. Drying in vacuo at 63° C. for 20 minutes gave 2-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-ethylamine as a light yellow foam resulted (0.775 g, 57.0%). Methanol and ethereal hydrochloride were added. Drying in vacuo for 16 hours 68° C. yielded the hydrochloride as a yellow foam (0.825 g). Mass spectrum (−EI, [M−H]−) m/z 366. 1HNMR (500 MHz, DMSO-d6): δ14.22 (s, 1H), 8.75 (d, 1H, J=8.66 Hz), 8.51-8.53 (m, 1H), 8.27 (d, 1H, J=8.29 Hz), 8.10 (s, br, 3H), 8.03-8.05 (m, 1H), 7.71-7.75 (m, 1H), 7.56-7.65 (m, 3H), 7.33 (d, 1H, J=2.19 Hz), 7.13-7.16 (m, 1H), 4.21 (t, 2H, J=5.00 Hz), 3.23 ppm (s, 2H). Elemental Analysis for C19H17N3O3S.1.00 mol HCl.0.55 mol H2O: Calcd: C, 55.15; H, 4.65; N, 10.15; Found: C, 55.54; H, 4.90; N, 10.12.

Workup

  1. filtrationIt was then filtered over Celite
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography with 0.5% ammonium hydroxide/5.0% methanol in chloroform
  4. customDrying in vacuo at 63° C. for 20 minutes

Sources & evidence

ORD record
ord-354b2fffc8bf4c69a3199daf56751e74
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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