Sodium Azide → 2-[4-Chloro-2-(2H-tetrazol-5-yloxy)-phenoxy]-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

HRID 11724Notes

Reaction equation

HRID 11724 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][C@H:11]2[CH3:24])=[O:9])=[C:4]([O:27][C:28]#[N:29])[CH:3]=1.[N-:30]=[N+:31]=[N-:32].[Na+]>CC(C)=O.O>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][C@H:11]2[CH3:24])=[O:9])=[C:4]([O:27][C:28]2[N:30]=[N:31][NH:32][N:29]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 696553652-(4-Chloro-2-cyanato-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

Product 1

HCID 696555952-[4-Chloro-2-(2H-tetrazol-5-yloxy)-phenoxy]-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(4-chloro-2-cyanato-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R)-2-methyl-piperazin-1-yl]-ethanone (0.17 g, 0.427 mmol) in acetone (2 mL) was added sodium azide (0.061 g, 0.94 mmol) and the reaction was stirred at reflux for 3 hours, then cooled to ambient temperature and stirred 18 hours. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The product was purified by anion exchange chromatography to give the title compound as its acetic acid addition salt (0.073 g, LRMS: 461.2, 463.3).

Workup

  1. temperatureat reflux for 3 hours
  2. stirringstirred 18 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by anion exchange chromatography

Sources & evidence

ORD record
ord-17657268a1964221876e8cddeab64dcb
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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