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1,1'-Carbonyldiimidazole → 3-(4-Fluorophenyl)-5-[2-(2-chlorophenyl)propionylamino]-4-[4-pyrimidinyl]isoxazole

HRID 547451
Notes
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Reaction equation

HRID 547451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([OH:11])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.C1CCN2C(=NCCC2)CC1.[NH2:36][C:37]1[O:41][N:40]=[C:39]([C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=2)[C:38]=1[C:49]1[CH:54]=[CH:53][N:52]=[CH:51][N:50]=1>C1COCC1>[F:48][C:45]1[CH:46]=[CH:47][C:42]([C:39]2[C:38]([C:49]3[CH:54]=[CH:53][N:52]=[CH:51][N:50]=3)=[C:37]([NH:36][C:9](=[O:11])[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH3:12])[O:41][N:40]=2)=[CH:43][CH:44]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 126365742-(2-Chlorophenyl)propanoic acidHCID 574677255-Amino-3-(4-fluorophenyl)-4-(4-pyrimidinyl)isoxazole

Product 1

HCID 671981653-(4-Fluorophenyl)-5-[2-(2-chlorophenyl)propionylamino]-4-[4-pyrimidinyl]isoxazoleYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 5 mL of THF, 0.144 g of 2-(2-chlorophenyl)propionic acid and 0.126 g of CDI were dissolved and stirred at room temperature for an hour. Then 5 mL of THF solution containing 0.237 g of DBU and 0.1 g of 5-amino-3 (4-fluorophenyl)-4-4-pyrimidinyl isoxazole was added and stirred at room temperature for 3 hours. The solvent was distilled off from the reaction solution under reduced pressure, and water was added to the residue which was then extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate, removed of the solvent by distillation under reduced pressure, and the residue was purified on 20 g silica gel chromatography (eluent, chloroform:methanol=50:1). Washing the residue with ether, 0.118 g (yield: 72%) of the title compound was obtained.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 3 hours
  3. distillationThe solvent was distilled off from the reaction solution under reduced pressure, and water
  4. additionwas added to the residue which
  5. extractionwas then extracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. customremoved of the solvent by distillation under reduced pressure
  9. customthe residue was purified on 20 g silica gel chromatography (eluent, chloroform:methanol=50:1)
  10. washWashing the residue with ether

Sources & evidence

ORD record
ord-1b57d0a242b54c36b1443860f70eb618
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07939536B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes