1H-Pyrazole, 5-[(3,3-difluoro-1-azetidinyl)methyl]-1-methyl-3-nitro- → HCID 86661233, compound

HRID 1918903Notes

Reaction equation

HRID 1918903 reaction equation
[F:1][C:2]1([F:16])[CH2:5][N:4]([CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)[CH2:3]1>C(O)C>[F:16][C:2]1([F:1])[CH2:5][N:4]([CH2:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([NH2:13])[CH:8]=2)[CH2:3]1

Participants

3

Reactant 1

HCID 866612321H-Pyrazole, 5-[(3,3-difluoro-1-azetidinyl)methyl]-1-methyl-3-nitro-

Product 1

HCID 86661233HCID 86661233, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A Parr reactor bottle was purged with nitrogen and charged with 10% palladium on carbon (30% wet, 150 mg dry weight) and a solution of 156e (1.78 mmol) in ethanol (25 mL). The bottle was attached to a Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 40 psi and shaken for 2 h. After this time, the hydrogen was evacuated, and the reaction mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×25 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford a quantitative yield of 156f (360 mg) as yellow oil: MS (ESI+) m/z 203.1 (M+H).

Workup

  1. customA Parr reactor bottle was purged with nitrogen
  2. additioncharged with 10% palladium on carbon (30% wet, 150 mg dry weight)
  3. customevacuated
  4. additioncharged with hydrogen gas to a pressure of 40 psi
  5. customAfter this time, the hydrogen was evacuated
  6. filtrationthe reaction mixture was filtered through a pad of Celite 521
  7. washThe filter cake was washed with ethanol (2×25 mL)
  8. concentrationthe combined filtrates were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4cc493a3cd5746828f98f14306921272
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…