Phenylacetyl chloride → HCID 15513074, compound

HRID 1635919Notes

Reaction equation

HRID 1635919 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[NH:4][N:3]=1.C(N(CC)CC)C.[C:27]1([CH2:33][C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH-].[Na+]>O1CCCC1.CO.O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[NH:4][N:3]=[C:2]([NH:1][C:34](=[O:35])[CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:6]=2[C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 155131015-(4-Fluorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-amine

Product 1

HCID 15513074HCID 15513074, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

254 mg of 3-amino-5-(4-fluorophenyl)-4-(4-pyridyl)pyrazole was suspended in 20 ml of tetrahydrofuran, and 306 mg of triethylamine was added thereto. Then, 5 ml of a tetrahydrofuran solution containing 464 mg of phenylacetyl chloride was added dropwise thereto, followed by stirring at room temperature for 3 hours. After the addition of water, the reaction mixture was extracted with ethyl acetate. After the organic layer was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. After the resulting residue was dissolved in a mixture composed of 20 ml of methanol and 2 ml of a 2 mol/L sodium hydroxide solution and stirred for 1 hour, the precipitated crystals were collected by filtration. Moreover, the crystals thus obtained were suspended in a mixture composed of 20 ml of methanol and 2 ml of a 2 mol/L sodium hydroxide solution, and heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure and then purified by column chromatography using 20 g of silica gel [with an elution solvent comprising chloroform-methanol (30:1)]. Thus, 80 mg (22% yield) of the title compound was obtained as colorless crystals.

Workup

  1. additionwas added dropwise
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washAfter the organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionAfter the resulting residue was dissolved in a mixture
  7. stirringstirred for 1 hour
  8. filtrationthe precipitated crystals were collected by filtration
  9. customMoreover, the crystals thus obtained
  10. temperatureheated
  11. temperatureunder reflux for 5 hours
  12. concentrationThe reaction mixture was concentrated under reduced pressure
  13. custompurified by column chromatography

Sources & evidence

ORD record
ord-8a21a643dd37434f9257c22e1ab614d2
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

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