1,1'-Carbonyldiimidazole → HCID 67196384, compound

HRID 547446Notes

Reaction equation

HRID 547446 reaction equation
[CH:1]1N=C[N:3]([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=O)[CH:2]=1.C1CCN2C(=NCCC2)CC1.[NH2:24][C:25]1[O:29][N:28]=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)C=1C1N=CC=CN=1.[CH3:43][O:44][CH2:45][O:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[CH2:53][C:54](O)=[O:55]>C1COCC1>[F:36][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[C:10]([C:9]3[CH:1]=[CH:2][N:3]=[CH:6][N:8]=3)=[C:25]([NH:24][C:54](=[O:55])[CH2:53][C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=3[O:46][CH2:45][O:44][CH3:43])[O:29][N:28]=2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20324415HCID 20324415, compoundHCID 67196561HCID 67196561, compound

Product 1

HCID 67196384HCID 67196384, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 16 mL of THF, 047 g of (2-methoxymethoxyphenyl)acetic acid and 0.5 g of CDI were dissolved and stirred at room temperature for 2 hours. Then 16 mL of a THF solution containing 0.92 g of DBU and 0.31 g of 5-amino-3-(4-fluorophenyl)-4-pyrimidinyl isoxazole was added, followed by 21 hours' stirring at room temperature. From the reaction solution the solvent was distilled off under reduced pressure. To the residue water was added and extracted with ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate and removed of the solvent by distillation under reduced pressure. The residue was purified on 50 g silica gel chromatography (eluent, chloroform:methanol=100:1) and the residue was washed with ether-hexane to provide 0.32 g yield: 60%) of the title compound.

Workup

  1. additionwas added
  2. waitfollowed by 21 hours
  3. stirring' stirring at room temperature
  4. distillationFrom the reaction solution the solvent was distilled off under reduced pressure
  5. additionTo the residue water was added
  6. extractionextracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. customremoved of the solvent by distillation under reduced pressure
  10. customThe residue was purified on 50 g silica gel chromatography (eluent, chloroform:methanol=100:1)
  11. washthe residue was washed with ether-hexane

Sources & evidence

ORD record
ord-872f7f0e17e443c0a631c3a9dfd7024f
Source dataset
uspto-grants-2011_05
Patent number
US07939536B2

Reaction notes

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