5-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole → 5-(Azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-amine

HRID 1918980Notes

Reaction equation

HRID 1918980 reaction equation
[N:1]1([CH2:5][C:6]2[N:10]([CH3:11])[N:9]=[C:8]([N+:12]([O-])=O)[CH:7]=2)[CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[N:1]1([CH2:5][C:6]2[N:10]([CH3:11])[N:9]=[C:8]([NH2:12])[CH:7]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 585403155-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole

Product 1

HCID 585400285-(Azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following Example 156f, 10% palladium on carbon (30% wet, 480 mg dry weight) and a solution of 200a (1.6 g, 8 mmol) in ethanol (50 mL) were reacted. The reaction mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×30 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford 5-(azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-amine 200b (quantitative) as yellow oil. MS (ESI+) m/z 167.1 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite 521
  2. washThe filter cake was washed with ethanol (2×30 mL)
  3. concentrationthe combined filtrates were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-055dfcfc1685453694b681ccf45cda0e
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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