Ethanol → HCID 135774068, compound

HRID 1958367Notes

Reaction equation

HRID 1958367 reaction equation
[C:1]([C:3]1[C:7]([CH3:8])=[N:6][N:5]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[C:4]=1[NH:19][C:20](=O)[CH3:21])#[N:2].C([OH:25])C.[OH-].[K+].OO>O.CO.C(O)(=O)C>[CH3:18][S:15]([C:12]1[CH:13]=[CH:14][C:9]([N:5]2[C:4]3[N:19]=[C:20]([CH3:21])[NH:2][C:1](=[O:25])[C:3]=3[C:7]([CH3:8])=[N:6]2)=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

8

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14797Potassium Hydroxide2×HCID 21897749HCID 21897749, compound

Product 1

HCID 135774068HCID 135774068, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

In to a 50 mL round-bottomed equipped with a stir bar and a reflux condenser was added, N-[4-cyano-2-(4-methanesulfonyl-phenyl)-5-methyl-2H-pyrazol-3-yl]-acetamide (30 mg, 0.079 mmol), H2O (0.6 mL), and ethanol (1 mL) followed by 20% aqueous KOH (0.33 mL). The reaction mixture turned purple and the solid dissolved after addition of KOH. Hydrogen peroxide (0.25 mL) was then added to the above solution. After stirring 15 min at room temperature, the reaction mixture was heated at 75° C. overnight. After cooled to room temperature acetic acid was added slowly until the pH attained a range between 6-6.5. The mixture was then diluted with H2O and methanol. The resulting precipitate was collected by filtration and washed with H2O, methanol, diethyl ether and dried under vacuum. The crude product was used directly in the next step without further purification. 1H NMR (DMSO-d6, 400 MHz) δ 1.71 (s, 2H), 2.39 (s, 3H), 2.51 (s, 1H), 3.25 (s, 3H), 8.05 (d, 2H), 8.46 (d, 2H). LCMS: calculated C14H14N4O3S 318.08, observed 319.1 (MH+)

Workup

  1. customIn to a 50 mL round-bottomed equipped with a stir bar and a reflux condenser
  2. additionwas added
  3. dissolutionthe solid dissolved
  4. temperaturethe reaction mixture was heated at 75° C. overnight
  5. additionwas added slowly until the pH
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with H2O, methanol, diethyl ether
  8. customdried under vacuum
  9. customThe crude product was used directly in the next step without further purification

Sources & evidence

ORD record
ord-f30ade166170498dae2cd7e518fd30f9
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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