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Imidazole → 3-(4-Fluorophenyl)-5-(phenylacetylamino)-4-(4-pyrimidinyl)isoxazole

HRID 547444
Notes
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Reaction equation

HRID 547444 reaction equation
N1C=CN=C1.C1CCN2C(=NCCC2)CC1.[C:17]1([CH2:23][C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH2:27][C:28]1[O:32][N:31]=[C:30]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[C:29]=1[C:40]1[CH:45]=[CH:44][N:43]=[CH:42][N:41]=1>C1COCC1>[F:39][C:36]1[CH:37]=[CH:38][C:33]([C:30]2[C:29]([C:40]3[CH:45]=[CH:44][N:43]=[CH:42][N:41]=3)=[C:28]([NH:27][C:24](=[O:25])[CH2:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:32][N:31]=2)=[CH:34][CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 7679Phenylacetyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 574677255-Amino-3-(4-fluorophenyl)-4-(4-pyrimidinyl)isoxazole

Product 1

HCID 574677243-(4-Fluorophenyl)-5-(phenylacetylamino)-4-(4-pyrimidinyl)isoxazoleYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Imidazole 0.43 g and DBU 1.9 g were dissolved in 40 mL of THF. Under cooling with ice, 0.97 g of phenylacetyl chloride was dropped into the solution, followed by 20 minutes' stirring at room temperature. Then 40 mL of a THF solution containing 0.8 g of 5-amino-3-(4-fluorophenyl)-4-(4-pyrimidinyl)isoxazole was dropped into the system and stirred at room temperature for 6 hours. From the reaction solution the solvent was distilled off under reduced pressure and water was added to the residue, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and from which the solvent was distilled off under reduced pressure. Thus obtained residue was purified on 40 g silica gel column chromatography (eluent, chloroform:methanol=100:1) and washed with ether to provide 0.77 g of the title compound (yield: 66%) in the form of colorless crystal.

Workup

  1. additionwas dropped into the solution
  2. additionwas dropped into the system
  3. stirringstirred at room temperature for 6 hours
  4. distillationFrom the reaction solution the solvent was distilled off under reduced pressure and water
  5. additionwas added to the residue, which
  6. extractionwas then extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate and from which the solvent
  8. distillationwas distilled off under reduced pressure
  9. customThus obtained residue was purified on 40 g silica gel column chromatography (eluent, chloroform:methanol=100:1)
  10. washwashed with ether

Sources & evidence

ORD record
ord-97b6824d721f4a4aa425a660e7f1ebef
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07939536B2

Reaction notes

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