Triethylamine → HCID 58270765, compound

HRID 222238Notes

Reaction equation

HRID 222238 reaction equation
[NH2:1][C:2](=[N:16][OH:17])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[F:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([F:28])[CH:27]=1)[C:22](Cl)=O.C(N(CC)CC)C.C(OCC)(=O)C>C1COCC1.O>[F:18][C:19]1[CH:20]=[C:21]([C:22]2[O:17][N:16]=[C:2]([CH:3]3[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:7][CH2:8]3)[N:1]=2)[CH:25]=[C:26]([F:28])[CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 1456003,5-Difluorobenzoyl chlorideHCID 54001703HCID 54001703, compound

Product 1

HCID 58270765HCID 58270765, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[amino(hydroxyimino)methyl]piperidine-1-carboxylate (3.0 g) in THF (30 mL) were added 3,5-difluorobenzoyl chloride (2.4 g) and triethylamine (3.44 mL) under ice-cooling, followed by stirring at room temperature for 2 hours. To the reaction liquid were added ethyl acetate and water, and the organic phase was separated. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the residue were added THF (25 mL) and a 1 M tetrabutylammonium fluoride/THF solution (12.4 mL), followed by stirring at 50° C. for 30 minutes. The reaction liquid was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform). To the purified product was added diisopropyl ether, and the resulting solid was collected by filtration and dried to obtain tert-butyl 4-[5-(3,5-difluorophenyl)-1,2,4-oxadiazol-3-yl]piperidine-1-carboxylate (4.22 g) as an orange solid.

Workup

  1. temperaturecooling
  2. customTo the reaction liquid
  3. customthe organic phase was separated
  4. washThe organic phase was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additionTo the residue were added THF (25 mL)
  8. stirringby stirring at 50° C. for 30 minutes
  9. customThe reaction liquid
  10. concentrationwas concentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (chloroform)
  12. additionTo the purified product was added diisopropyl ether
  13. filtrationthe resulting solid was collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-a047debf593a42438686d46ca02ad00b
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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