HCID 68458276, compound → HCID 68457327, compound

HRID 2356845Notes

Reaction equation

HRID 2356845 reaction equation
C(OC(=O)[NH:10][CH:11]([C:13](=[O:37])[NH:14][C:15]1[N:16]([C:33]([CH3:36])([CH3:35])[CH3:34])[N:17]=[C:18]([C:20]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)[CH:19]=1)[CH3:12])C1C=CC=CC=1>CCO.[Pd]>[NH2:10][CH:11]([CH3:12])[C:13]([NH:14][C:15]1[N:16]([C:33]([CH3:36])([CH3:35])[CH3:34])[N:17]=[C:18]([C:20]2([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]2)[CH:19]=1)=[O:37]

Participants

4

Reactant 1

HCID 68458276HCID 68458276, compound

Product 1

HCID 68457327HCID 68457327, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 0.36 g (0.7 mmol) of {1-[2-tert-butyl-5-(1-methyl-4-phenylpiperidin-4-yl)-2H-pyrazol-3-ylcarbamoyl]ethyl}carbamic acid benzyl ester and 0.36 g of 10% Pd/C in 5.0 mL of absolute EtOH was agitated under 30 psi H2 for 16 h. The reaction mixture was filtered through Celite and 0.36 g of fresh 10% Pd/C was added to the filtrate which was again agitated under 30 psi H2 for 16 h. This process was repeated once more and, after a final filtration, the filtrate was concentrated. Purification on silica gel using 4% Et3N-MeOH as eluant afforded 2-amino-N-[2-tert-butyl-5-(1-methyl-4-phenylpiperidin-4-yl)-2H-pyrazol-3-yl]propionamide.

Workup

  1. filtrationThe reaction mixture was filtered through Celite and 0.36 g of fresh 10% Pd/C
  2. additionwas added to the filtrate which
  3. stirringwas again agitated under 30 psi H2 for 16 h
  4. filtrationafter a final filtration
  5. concentrationthe filtrate was concentrated
  6. customPurification on silica gel using 4% Et3N-MeOH as eluant

Sources & evidence

ORD record
ord-5d46bcafbd1247ff94d0b54c6f383430
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

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