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

HRID 337299Notes

Reaction equation

HRID 337299 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>C(O)C.[Pd]>[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-amineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-(azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole (349 mg, 1.78 mmol) in ethanol (20 mL) was treated with palladium on carbon (10%, 50 mg). The resulting mixture was stirred under a hydrogen (1 atm) for 48 h. The reaction mixture was filtered through a celite pad, and the pad washed with ethanol. The filtrate was concentrated in vacuo to give 5-(azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-amine (292 mg, 99%) as a light yellow oil. 1H NMR (300 MHz, DMSO-d6) 8 ppm 1.93 (quin, J=6.89 Hz, 2 H) 3.06 (t, J=6.99 Hz, 4 H) 3.34 (s, 2 H) 3.46 (s, 3 H) 4.36 (s, 2 H) 5.25 (s, 4 H).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washthe pad washed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-50c5b94320224dde88aea6ec77972338
Source dataset
uspto-grants-2014_11
Patent number
US08889682B2

Reaction notes

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