5-(1-azido-2-ethylbutyl)-1-(4-methoxybenzyl)-1H-pyrazole → {2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butyl}amine

HRID 748038Notes

Reaction equation

HRID 748038 reaction equation
[N:1]([CH:4]([C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:13]=[CH:12][CH:11]=1)[CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])=[N+]=[N-]>CO.[Pd]>[CH2:8]([CH:5]([CH2:6][CH3:7])[CH:4]([NH2:1])[C:10]1[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[N:13]=[CH:12][CH:11]=1)[CH3:9]

Participants

4

Reactant 1

HCID 866000025-(1-azido-2-ethylbutyl)-1-(4-methoxybenzyl)-1H-pyrazole

Product 1

HCID 68593849{2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butyl}amineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(1-Azido-2-ethylbutyl)-1-(4-methoxybenzyl)-1H-pyrazole (0.750 g, 2.39 mmol) in MeOH (24 mL) with 5% Pd/C (75 mg) was hydrogenated under atm pressure for 24 h. The reaction mixture was filtered through a plug of Celite and the filtrate was concentrated to give 0.637 g (93%) of {2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butyl}amine as an oil.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-91717fe08b104fca87d4805af4f62d9f
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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