Hydrochloric Acid → HCID 178446887, compound

HRID 1359196Notes

Reaction equation

HRID 1359196 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16]=3[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[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+].Cl>CN(C=O)C.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[O:13][C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16]=1[C:17](=[O:22])[CH2:18][CH2:19][CH2:20][CH3:21])=[CH:7]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 114198352-{[1-Bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile

Product 1

HCID 178446887HCID 178446887, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile (0.488 g, 1.06 mmol), sodium azide (0.347 g, 5.34 mmol), ammonium chloride (0.289 g, 5.40 mmol) in DMF (10 ml) was heated to 80° C. for 2 hours. The reaction mixture was allowed to cool to room temperature. It was poured into excess water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and brine. It was dried over anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by HPLC using 0.1% TFA in 80% acetonitrile/20% water as the mobile phase. The acetonitrile was evaporated and the residue was extracted with ethyl acetate The extract was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The solid was dried at 90° C. for 11 hours affording the title compound as a light yellow solid (0.232 g), m184-185° C. Mass spectrum (+APCl, [M+H]+) m/z 505. 1HNMR (400 MHz, DMSO-d6): δ16.8-17.2 (br s, 1H), 8.5 (d, 1H, J=1.7 Hz), 8.25 (t, 2H, J=9.1 Hz), 8.0-8.05 (m, 2H), 7.75-7.8 (m, 2H), 7.4-7.5 (m, 2H), 5.8 (s, 2H), 2.75 (t, 2H, J=7.3 Hz), 1.5-1.6 (m, 2H), 1.1-1.2 (m, 2H), and 0.7 ppm (t, 3H, J=7.3 Hz). Elemental Analysis for C25H21, BrN4O3: Calculated: C, 59.42; H, 4.19; N, 11.09. Found: C, 59.03; H, 3.98; N, 10.75.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialIt was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customThe residue was purified by HPLC
  8. customThe acetonitrile was evaporated
  9. extractionthe residue was extracted with ethyl acetate The extract
  10. washwas washed with water and brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe solid was dried at 90° C. for 11 hours

Sources & evidence

ORD record
ord-be328d072a734a788bab7db6fc95ae91
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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