Hydrochloric Acid → HCID 178446889, compound

HRID 1373873Notes

Reaction equation

HRID 1373873 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][CH:23]([CH3:25])[CH3:24])=[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][CH:23]([CH3:25])[CH3:24])=[CH:7]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21075898HCID 21075898, compound

Product 1

HCID 178446889HCID 178446889, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of {1-bromo-6-[3-(3-methyl-butyryl)-benzo[b]thiophen-2-yl]-naphthalen-2-yloxy}-acetonitrile (1.01 g, 2.11 mmol), sodium azide (0.687 g, 10.6 mmol) and ammonium chloride (0.570 g, 10.7 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. Drying in vacuo at 78° C. for 12 hours yielded 1-{2-[5-bromo-6-(1H-tetrazol-5-ylmethoxy)-naphthalen-2-yl]-benzo[b]thiophen-3-yl}-3-methyl-butan-1-one as a yellow foam (0.602 g, 75%). Mass spectrum (+EI, [M+H]+) m/z 521/523. 1H NMR (500 MHz, DMSO-d6): δ16.7–17.2 (br, 1H), 8.24 (d, 1H, J=9.01 Hz), 8.16–8.19 (m, 2H), 8.08–8.10 (m, 1H), 7.95–7.97 (m, 1H), 7.75–7.79 (m, 2H), 7.46–7.52 (m, 2H), 5.77 (s, 2H), 2.32 (d, 2H, J=6.72 Hz), 1.95–2.02 (m, 1H), 0.65 ppm (d, 6H, J=6.57 Hz). Elemental Analysis for C25H21BrN4O2S: Calcd: C, 57.59; H, 4.06; N, 10.74; Found: C, 57.37; H, 4.12; N, 10.48.

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. customDrying in vacuo at 78° C. for 12 hours

Sources & evidence

ORD record
ord-196c9113758744eba95bdec744b1e427
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

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