Hydrochloric Acid → HCID 178446890, compound

HRID 1373863Notes

Reaction equation

HRID 1373863 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:26])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:27][CH2:28][C:29]#[N:30].[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-].[NH4+].CN(C=O)C.Cl>O>[Br:1][C:2]1[C:3]([O:27][CH2:28][C:29]2[NH:33][N:32]=[N:31][N:30]=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:26])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:7]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21075899HCID 21075899, compound

Product 1

HCID 178446890HCID 178446890, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of [1-bromo-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetonitrile (0.576 g, 1.20 mmol), sodium azide (0.393 g, 6.05 mmol) and ammonium chloride (0.33 g, 6.2 mmol) in DMF (10 mmol) was heated at 80° C. for three 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 81% acetonitrile (0.1% formic 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 58° C. for 16 hours yielded 1-{2-[5-bromo-6-(1H-tetrazol-5-ylmethoxy)-naphthalen-2-yl]-benzo[b]thiophen-3-yl}-pentan-1-one as a light yellow foam (0.312 g, 49.8%). Mass spectrum (+EI, [M+H]+) m/z 521/523. 1H NMR (500 MHz, DMSO-d6): δ16.6–17.3 (br, 1H), 8.24 (d, 1H, J=8.86 Hz),8.16–8.20 (m, 2H), 8.08–8.09 (m, 1H), 7.95–7.97 (m, 1H), 7.75–7.78 (m, 2H), 7.46–7.52 (m, 2H), 5.76 (s, 2H), 2.42 (t, 2H, J=7.26 Hz), 1.40–1.46 (m, 2H), 0.96–1.04 (m, 2H), 0.58 ppm (t, 3H, J=7.42 Hz). Elemental Analysis for C25H21BrN4O2S: Calcd: C, 57.59; H, 4.06; N, 10.74; Found: C, 57.42; H, 4.19; N, 10.59.

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 58° C. for 16 hours

Sources & evidence

ORD record
ord-913e63661b544bf2844b19a429af0e34
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

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