Water → HCID 178514588, compound

HRID 2240012Notes

Reaction equation

HRID 2240012 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]1([S:15]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH2:30]OS(C4C=CC(C)=CC=4)(=O)=O)[CH:25]=3)[NH:20][N:19]=2)(=[O:17])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.O>CN(C=O)C>[N:1]([CH2:30][CH2:29][CH2:28][O:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[C:18]2[S:15]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)(=[O:16])=[O:17])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 178427737HCID 178427737, compound

Product 1

HCID 178514588HCID 178514588, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium azide (0.425 g, 6.54 mmol) was added to a solution of toluene-4-sulfonic acid 3-[3-(naphthalene-1-sulfonyl)-1H-indazol-5-yloxy]-propyl ester (1.16 g, 2.16 mmol) in DMF (20 mL). The reaction mixture was stirred at 80° C. for 15 hours in a sealed tube. After cooling to ambient temperature, it was poured into excess water and extracted with ethyl acetate. The organic phase was washed with 10% ammonium chloride/water solution, water and brine. It was dried with anhydrous magnesium sulfate, filtered, concentrated and dried at 73° C. in vacuo for 45 minutes to yield 5-(3-azido-propoxy)-3-(naphthalene-1-sulfonyl)-1H-indazole as an amber gum (0.770 g, 87.7%); Mass Spectrum (−EI, [M−H]−) m/z 406. 1HNMR (400 MHz, DMSO-d6): δ14.05 (br, 1H), 8.64-8.68 (m, 1H), 8.53 (dd, 1H, J=7.42 Hz and 1.16 Hz), 8.25-8.28 (m, 1H), 8.01-8.05 (m, 1H), 7.70-7.74 (m, 1H), 7.52-7.64 (m, 3H), 7.26 (d, 1H, J=2.08 Hz), 7.08 (dd, 1H, J=9.16 Hz and 2.32 Hz), 4.06 (t, 2H, J=6.14 Hz), 3.49-3.52 (m, 2H), 1.96-1.99 ppm (m, 2H).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with 10% ammonium chloride/water solution, water and brine
  4. dry with materialIt was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried at 73° C. in vacuo for 45 minutes

Sources & evidence

ORD record
ord-677cc4a9cbb44e4e8695064890df682e
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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