Ammonium Chloride → HCID 178505488, compound

HRID 561224Notes

Reaction equation

HRID 561224 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:15]=[C:14]([C:16]#[N:17])[O:13][N:12]=2)[CH2:7][CH2:6]1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+]>CN(C=O)C.[OH-].[Na+]>[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]2[N:15]=[C:14]([C:16]3[NH:25][N:24]=[N:23][N:17]=3)[O:13][N:12]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 66696816HCID 66696816, compound

Product 1

HCID 178505488HCID 178505488, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,2,4-oxadiazole-5-carbonitrile (8 g, 21.79 mmol), sodium azide (2.125 g, 32.7 mmol) and ammonium chloride (5.83 g, 109 mmol) in DMF (43.6 ml) was heated at 100° C. for 0.5 h. The mixture was cooled to RT, diluted with 1N NaOH (50 mL), washed with Et2O (2×50 mL). The aqueous layer was acidified to pH about 1 with 2N HCl and extracted with EtOAc (3×75 mL). The combined organic fractions were washed with water (2×50 mL) then dried over Na2SO4. The solvent was evaporated under reduced pressure, the product dissolved in a small amount of EtOAc and precipitated with hexanes. The solid was filtered and washed with hexanes to afford the title compound. MS: m/z 410, 412 (MH+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. washwashed with Et2O (2×50 mL)
  3. extractionextracted with EtOAc (3×75 mL)
  4. washThe combined organic fractions were washed with water (2×50 mL)
  5. dry with materialthen dried over Na2SO4
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionthe product dissolved in a small amount of EtOAc
  8. customprecipitated with hexanes
  9. filtrationThe solid was filtered
  10. washwashed with hexanes

Sources & evidence

ORD record
ord-9441051c884341139e31daa2daec0278
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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