Triethylamine → HCID 66696816, compound

HRID 561223Notes

Reaction equation

HRID 561223 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:15]=[C:14]([C:16]([NH2:18])=O)[O:13][N:12]=2)[CH2:7][CH2:6]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[Br:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]2[N:15]=[C:14]([C:16]#[N:18])[O:13][N:12]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 66696833HCID 66696833, compound

Product 1

HCID 66696816HCID 66696816, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,2,4-oxadiazole-5-carboxamide (11 g, 28.6 mmol) and triethylamine (12.74 ml, 91 mmol) in THF (95 ml) was added trifluoroacetic anhydride (6.05 mL, 42.8 mmol) dropwise at 0° C. The mixture was warmed to RT and stirred for a further 30 min. The solvent was evaporated and the residue was diluted with Et2O (50 mL) then with dilute NaHCO3 solution (100 mL). The aqueous layer was extracted with Et2O (3×100 mL). The combined organic fractions were dried over Na2SO4 and the solvent was evaporated under reduced pressure. Purification by Combiflash chromatography (SiO2-120 g, gradient elution of 10-30% EtOAc/hexanes over 25 min) afforded the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with Et2O (50 mL)
  3. extractionThe aqueous layer was extracted with Et2O (3×100 mL)
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customPurification
  7. washby Combiflash chromatography (SiO2-120 g, gradient elution of 10-30% EtOAc/hexanes over 25 min)

Sources & evidence

ORD record
ord-0a904d2088e64a9e9f0128baf666eaef
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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