Triethylamine → HCID 86680375, compound

HRID 83544Notes

Reaction equation

HRID 83544 reaction equation
CC1[N:3]([C:8]2[CH:12]=[C:11]([I:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:9]=2)C(C)=CC=1.[Cl-].O[NH3+].C(N(CC)CC)C>CCCCCC.C(OCC)(=O)C>[F:20][C:17]1[CH:16]=[CH:15][C:14]([N:10]2[C:11]([I:13])=[CH:12][C:8]([NH2:3])=[N:9]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21645Hydroxylamine HClHCID 86680376HCID 86680376, compound

Product 1

HCID 86680375HCID 86680375, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of 3-(2,5-dimethylpyrrol-1-yl)-1-(4-fluorophenyl)-5-iodo-1H-pyrazole (625 mg) in ethanol/water (2/1, 12.5 ml) were sequentially added hydroxylammonium chloride (2.28 g) and triethylamine (0.46 ml) at room temperature, and the mixture was stirred at 95° C. for 15 hours. This reaction mixture was cooled to room temperature, concentrated under reduced pressure. To the resulting residue was added a 8M aqueous solution of sodium hydroxide, and then the mixture was extracted with ethyl acetate. This organic layer was sequentially washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to give the titled compound (318 mg).

Workup

  1. customat room temperature
  2. temperatureThis reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionTo the resulting residue was added a 8M aqueous solution of sodium hydroxide
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThis organic layer was sequentially washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-e79e609dee64437a932e0d8e38630821
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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