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Water → HCID 69692723, compound

HRID 1635930
Notes
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Reaction equation

HRID 1635930 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)[N:4]([CH3:20])[N:3]=1.C(N(CC)CC)C.[C:28]1([CH2:34][C:35](Cl)=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>O1CCCC1>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[N:4]([CH3:20])[N:3]=[C:2]([NH:1][C:35](=[O:36])[CH2:34][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:6]=2[C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 18674082HCID 18674082, compound

Product 1

HCID 69692723HCID 69692723, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

Procedure

338 mg of 3-amino-5-(4-fluorophenyl)-1-methyl-4-(4-pyridyl)pyrazole was dissolved in 20 ml of a tetrahydrofuran, followed by the addition of 140 mg of triethylamine. Then, 5 ml of a tetrahydrofuran solution containing 214 mg of phenylacetyl chloride was added dropwise thereto, followed by stirring at room temperature overnight. After the addition of water, the reaction mixture was extracted with chloroform. After the organic layer was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography using 80 g of silica gel [with an elution solvent comprising chloroform-methanol (40:1)]. Thus, 310 mg (64% yield) of the title compound was obtained as pale-yellow crystals.

Workup

  1. additionwas added dropwise
  2. extractionthe reaction mixture was extracted with chloroform
  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. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-0c13352279af45d5b19752b24102cb06
Source dataset
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06511997B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes