1-{[5-(Benzyloxy)-1-methyl-1H-pyrazol-3-yl]carbonyl}-4-(2-tert-butylphenyl)piperazine → HCID 178481911, compound

HRID 535011Notes

Reaction equation

HRID 535011 reaction equation
C([O:8][C:9]1[N:13]([CH3:14])[N:12]=[C:11]([C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:19][CH2:18]2)=[O:16])[CH:10]=1)C1C=CC=CC=1>CO.[C].[Pd]>[C:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N:20]1[CH2:19][CH2:18][N:17]([C:15]([C:11]2[CH:10]=[C:9]([OH:8])[N:13]([CH3:14])[N:12]=2)=[O:16])[CH2:22][CH2:21]1)([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 1

HCID 667928171-{[5-(Benzyloxy)-1-methyl-1H-pyrazol-3-yl]carbonyl}-4-(2-tert-butylphenyl)piperazine

Product 1

HCID 178481911HCID 178481911, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-{[5-(benzyloxy)-1-methyl-1H-pyrazol-3-yl]carbonyl}-4-(2-tert-butylphenyl)piperazine (1.75 g), and palladium-carbon (500 mg) in methanol (150 mL) was stirred under hydrogen atmosphere (5 atm). The mixture was filtered and concentrated under reduced pressure to purify the residue by silica gel column chromatography (ethyl acetate/methanol 100:0 to 90:10). Solvent was removed to obtain a solid (650 mg, 56%). LC/MS; ESI(+) m/z: 343 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customto purify the residue by silica gel column chromatography (ethyl acetate/methanol 100:0 to 90:10)
  4. customSolvent was removed

Sources & evidence

ORD record
ord-01f2658fd2184d1e969d62de0b420d67
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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