Acetic Acid → HCID 67384555, compound

HRID 1471887Notes

Reaction equation

HRID 1471887 reaction equation
C(OCC[N:11]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:12]1)C1C=CC=CC=1.[C:22](O)(=[O:24])[CH3:23]>C1COCC1.[Pd]>[C:16]1([C:13]2[CH:14]=[C:15]([CH2:23][CH2:22][OH:24])[NH:11][N:12]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86657579HCID 86657579, compound

Product 1

HCID 67384555HCID 67384555, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-(2-(Benzyloxy)ethyl-3-phenyl-1H-pyrazole (2.1 g, 7.54 mmol) was dissolved in acetic acid (10 mL) and THF (10 mL). Palladium on carbon (0.080 g, 0.754 mmol) was added and the reaction was stirred for 4 days under hydrogen atmosphere on the Parr shaker at 55 psi. After this time, the reaction was filtered through celite and washed with EtOAc. The solvents were evaporated. The reaction progress was checked by TLC and shown to be ˜50-60% complete. The reaction was set up on the Parr shaker again. After three more days on the Parr shaker, the reaction was stopped. The reaction was filtered through celite and the solvents removed. The reaction was extracted (70 mL each of H2O and EtOAc). The aqueous layer was extracted again with EtOAc (70 mL). The combined organic layer was dried and concentrated, and the residue was purified by column chromatography to give the title compound (665 mg) as a white solid. LCMS m/z=189.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.68-2.82 (m, 2H), 3.60-3.71 (m, 2H), 4.73-4.81 (m, 1H), 6.48 (s, 1H), 7.20-7.49 (m, 3H), 7.55-7.96 (m, 2H), 12.53 (s, 1H).

Workup

  1. filtrationAfter this time, the reaction was filtered through celite
  2. washwashed with EtOAc
  3. customThe solvents were evaporated
  4. filtrationThe reaction was filtered through celite
  5. customthe solvents removed
  6. extractionThe reaction was extracted (70 mL each of H2O and EtOAc)
  7. extractionThe aqueous layer was extracted again with EtOAc (70 mL)
  8. customThe combined organic layer was dried
  9. concentrationconcentrated
  10. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3c57ffaeded141ce84e52249b2b9159d
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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