HCID 90030086, compound → HCID 178494717, compound

HRID 1488183Notes

Reaction equation

HRID 1488183 reaction equation
C([N:8]1[CH:12]=[C:11]([CH3:13])[C:10]([CH2:14][O:15][CH3:16])=[N:9]1)C1C=CC=CC=1>CO>[CH3:16][O:15][CH2:14][C:10]1[C:11]([CH3:13])=[CH:12][NH:8][N:9]=1

Participants

3

Reactant 1

HCID 90030086HCID 90030086, compound2×

Product 1

HCID 178494717HCID 178494717, compoundYield 122.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of 1-benzyl-3-(methoxymethyl)-4-methyl-1H-pyrazole (compound 268.3, 700 mg, 3.24 mmol) in methanol (10 mL). The system was purged with nitrogen, then Pd(OH)2/C (70 mg, 20 wt %) and aqueous HCl (2 M, 0.3 mL) were carefully added. The system was then charged with hydrogen (1 atm) and the resulting mixture was stirred for 2 days at room temperature. The system was purged with nitrogen, then the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The pH of the residue was adjusted to 7 with aqueous sodium bicarbonate (sat.) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine (2×30 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the title compound as a yellow oil (500 mg, crude).

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customThe system was purged with nitrogen
  3. additionPd(OH)2/C (70 mg, 20 wt %) and aqueous HCl (2 M, 0.3 mL) were carefully added
  4. additionThe system was then charged with hydrogen (1 atm)
  5. customThe system was purged with nitrogen
  6. customthe solids were removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. extractionextracted with ethyl acetate (3×50 mL)
  9. washThe combined organic extracts were washed with brine (2×30 mL)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87476995edc4491dbf8760a925b8877a
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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