Acetic Acid → HCID 59738190, compound

HRID 561230Notes

Reaction equation

HRID 561230 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[N:17]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1.C(O)(=O)C.Cl>O1CCOCC1>[Br:1][C:2]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[N:17]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 66696822HCID 66696822, compound

Product 1

HCID 59738190HCID 59738190, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 3-(3-{3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)propanoate (75 mg, 0.148 mmol) in dioxane (492 μL) was added acetic acid (253 μL, 4.43 mmol) and conc. HCl (363 μL, 4.43 mmol). The mixture was heated at 90° C. for 1 h. The solvent was evaporated to one-third its volume, diluted with water (2 mL) and extracted with EtOAc (2×2 mL). The combined organic fractions were extracted with 1N NaOH (1 mL), the aqueous layer was acidified with 2N HCl (1 mL) and extracted with EtOAc (3×2 mL). The combined organic fractions were dried over Na2SO4 and the solvent was evaporated. The product was triturated with hexanes (2×2 mL) and dried under high vacuum to give the title compound.

Workup

  1. customThe solvent was evaporated to one-third its volume
  2. additiondiluted with water (2 mL)
  3. extractionextracted with EtOAc (2×2 mL)
  4. extractionThe combined organic fractions were extracted with 1N NaOH (1 mL)
  5. extractionextracted with EtOAc (3×2 mL)
  6. dry with materialThe combined organic fractions were dried over Na2SO4
  7. customthe solvent was evaporated
  8. customThe product was triturated with hexanes (2×2 mL)
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-f613debd84e44c96835249c48740358f
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

Loading…