HCID 67324388, compound → HCID 178448774, compound

HRID 1397461Notes

Reaction equation

HRID 1397461 reaction equation
C([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([C:19]([CH3:23])([CH3:22])[CH2:20][NH2:21])=[N:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:23][C:19]([C:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:8][N:9]=1)([CH3:22])[CH2:20][NH2:21]

Participants

4

Reactant 1

HCID 67324388HCID 67324388, compound

Product 1

HCID 178448774HCID 178448774, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

2-(1-Benzyl-5-phenyl-1H-pyrazol-3-yl)-2-methylpropan-1-amine (50 mg, 0.2 mmol) was stirred under an atmosphere of hydrogen in methanol/concentrated sulfuric acid (5:1, 5 mL) with 5% palladium on carbon (350 mg). After several h, more palladium on carbon was added (350 mg). The reaction was stopped after 3 days with starting material remaining. The solution was degassed and filtered through Celite. Methanol was removed under vacuum and 1 M potassium carbonate was added until the reaction was basic. The slurry was extracted multiple times with 30% isopropanol/chloroform. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to yield 2-methyl-2-(5-phenyl-1H-pyrazol-3-yl)propan-1-amine, which was carried through without further purification.

Workup

  1. customThe solution was degassed
  2. filtrationfiltered through Celite
  3. customMethanol was removed under vacuum and 1 M potassium carbonate
  4. additionwas added until the reaction
  5. extractionThe slurry was extracted multiple times with 30% isopropanol/chloroform
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e93760db321b4d72b1565f907b2428fe
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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