Sodium Hydroxide → HCID 135848073, compound

HRID 498053Notes

Reaction equation

HRID 498053 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1.CC[O:16][C:17]([CH:19]1[C:24](=O)[CH2:23][CH2:22][CH2:21][CH2:20]1)=O.[OH-].[Na+]>O>[CH3:1][C:2]1[C:6]2[C:17](=[O:16])[C:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[NH:7][C:5]=2[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 7351323-Methyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine

Product 1

HCID 135848073HCID 135848073, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of polyphosphoric acid (4.02 g) and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (1.75 g, 10.0 mmol) was heated at 130° C. The mixture was stirred at the same temperature, while ethyl 2-cyclohexanone carboxylate(1.70 mL, 10.6 mmol) was added thereto gradually. The mixture was stirred at the same temperature further for 4 hours. The solution was allowed to cool to room temperature, and water was added to the mixture. The solution was neutralized by the addition of a sodium hydroxide solution and the organic matter was extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform:methanol=100:1 to 50:1 to 20:1), and recrystallized from ethyl acetate to give the title compound (0.39 g, 14% yield).

Workup

  1. additionwas added
  2. temperatureto cool to room temperature
  3. extractionthe organic matter was extracted with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (chloroform:methanol=100:1 to 50:1 to 20:1)
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cce063f12aa04f85b2a8d2b03ceb72d5
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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