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

HRID 1520027Notes

Reaction equation

HRID 1520027 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>CO.[Ni]>[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 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(1-Methylpyrrolidin-3-yl)-4-nitro-1H-pyrazole (3.0 g, 18 mmol, 1 eq.) in methanol (40 mL) was hydrogenated (3 bars) in presence of Ra—Ni (1 g) at RT. After 3 h, the catalyst was filtered off and the filtrate was concentrated under reduced pressure to give the title compound as brown liquid. 1H NMR (400 MHz, DMSO-d6) δ 7.06 (s, 1H), 6.85 (m, 1H), 4.67 (m, 1H), 3.82 (brs, 2H) 2.63-2.74 (m, 2H), 2.58-2.61 (m, 1H), 2.38-2.44 (m, 1H), 2.21-2.28 (m, 1H), 2.27 (s, 3H), 1.89-1.97 (m, 1H).

Workup

  1. customat RT
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-402b9ea0308943319902400848df970c
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

Loading…