HCID 67981250, compound → 1-(1-Methyl-3-pyrrolidinyl)-1H-pyrazol-4-amine

HRID 592399Notes

Reaction equation

HRID 592399 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[N:8]2)[CH2:3]1>CCO.[Pd]>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH2:12])[CH:9]=[N:8]2)[CH2:3]1

Participants

4

Reactant 1

HCID 67981250HCID 67981250, compound

Product 1

HCID 679816411-(1-Methyl-3-pyrrolidinyl)-1H-pyrazol-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(1-methylpyrrolidin-3-yl)-4-nitro-1H-pyrazole A23 (0.575 g, 2.93 mmol) and 10% Pd/C (0.061 g) in EtOH (15 mL) was stirred under a hydrogen atmosphere for 16 hours. The reaction mixture was filtered through Celite and the solvent was removed in vacuo to give the title compound A24 as a red oil (0.555 g, quantitative). 1H NMR (300 MHz, MeOD) δ 2.27-2.42 (m, 1H), 2.72-2.76 (m, 2H), 3.02-3.10 (m, 1H), 3.46-3.55 (m, 1H), 3.70-3.85 (m, 4H), 5.14-5.26 (m, 1H), 7.33 (s, 1H), 7.46 (m, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2ac645e1682f41ddab2e14f322cc3a2e
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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