Hydrochloric Acid → HCID 178520206, compound

HRID 1373869Notes

Reaction equation

HRID 1373869 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[S:16][C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[C:13]=3[C:21](=[O:29])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:30][CH2:31][C:32]#[N:33].[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+].CN(C=O)C.Cl>O>[Br:1][C:2]1[C:3]([O:30][CH2:31][C:32]2[NH:36][N:35]=[N:34][N:33]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][C:8]([C:12]1[S:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[C:13]=1[C:21](=[O:29])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[CH:7]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21075900HCID 21075900, compound

Product 1

HCID 178520206HCID 178520206, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of [1-bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetonitrile (0.437 g, 0.852 mmol), sodium azide (0.284 g, 4.36 mmol) and ammonium chloride (0.233 g, 4.36 mmol) in DMF (10 mmol) was heated at 80° C. for two hours. After cooling to ambient temperature, the reaction mixture was poured into excess water and acidified with 2N hydrochloric acid. This was then extracted with ethyl acetate. The organic phase was washed with water and brine. It was then dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by HPLC using 72% acetonitrile (0.1% trifluoroacetic acid) in water as the mobile phase. Evaporating the solvent and extracting with ethyl acetate, washing with water and brine, drying with anhydrous magnesium sulfate, filtering, concentrating and drying in vacuo at 64° C. for four hours yielded 1-{2-[5-bromo-6-(1H-tetrazol-5-ylmethoxy)-naphthalen-2-yl]-benzo[b]thiophen-3-yl}-2-phenyl-ethanone as a yellow foam (0.180 g, 38.1%); mass spectrum (+EI, [M+H]+) m/z 555/557. 1H NMR (500 MHz, DMSO-d6): δ16.7–17.2 (br, 1H), 8.27 (d, 1H, J=8.86 Hz), 8.18–8.20 (m, 2H), 8.07–8.10 (m, 1H), 7.90–7.93 (m, 1H), 7.82 (dd, 1H, J=8.70 Hz and 1.83 Hz), 7.77 (d, 1H, J=9.16 Hz), 7.45–7.50 (m, 2H), 7.13–7.19 (m, 3H), 6.93 (dd, 2H, J=7.64 Hz and 1.55 Hz), 5.77 (s, 2H), 3.81 ppm (s, 2H). Elemental Analysis for C28H19BrN4O2S+0.3 mole H2O: Calcd: C, 59.96; H, 3.52; N, 9.99; Found: C, 59.58; H, 3.40; N, 9.69.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionThis was then extracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialIt was then dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customThe residue was purified by HPLC
  8. customEvaporating the solvent
  9. extractionextracting with ethyl acetate
  10. washwashing with water and brine
  11. dry with materialdrying with anhydrous magnesium sulfate
  12. filtrationfiltering
  13. concentrationconcentrating
  14. customdrying in vacuo at 64° C. for four hours

Sources & evidence

ORD record
ord-6ee5bb3f0e464d3d9d63fdc6c5fba995
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

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