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

HRID 748045Notes

Reaction equation

HRID 748045 reaction equation
[N:1]([CH:4]([C:10]1[N:14]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[N:13]=[CH:12][CH:11]=1)[CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])=[N+]=[N-]>[Pd]>[CH2:8]([CH:5]([CH2:6][CH3:7])[CH:4]([NH2:1])[C:10]1[N:14]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[N:13]=[CH:12][CH:11]=1)[CH3:9]

Participants

3

Reactant 1

HCID 866000035-(1-azido-2-ethylbutyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole

Product 1

HCID 68593832(2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butyl)amineYield 86.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 5-(1-azido-2-ethylbutyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole (0.260 g) and 5% Pd/C (16 mg) was stirred under an atm pressure of H2 for 15 h. The mixture was filtered through a plug of Celite and the solvent was removed in vacuo to give 0.207 g of (2-ethyl-1-{1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-5-yl}butyl)amine with an impurity present. This compound was used in the next step without purification.

Workup

  1. filtrationThe mixture was filtered through a plug of Celite
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1c8d69ebccc34f40bf098dd057aae515
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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