HCID 18510734, compound → HCID 69094655, compound

HRID 2219097Notes

Reaction equation

HRID 2219097 reaction equation
Cl.ClC(C#N)(C1C=CC=CC=1)C1C=CC([NH:10][C:11]([CH:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:14]2)=[O:12])=CC=1>CO>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:15]2[CH2:14][CH:13]([C:11]([NH2:10])=[O:12])[O:17][N:16]=2)[CH:19]=1

Participants

3

Reactant 1

HCID 18510734HCID 18510734, compound

Product 1

HCID 69094655HCID 69094655, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

) A solution of (±)-N-[4-(chlorocyanophenylmethyl)phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide monohydrochloride (0.004 mol) in methanol (50 ml) was stirred and refluxed for 30 minutes. The solvent was evaporated. The residue was purified by high-performance liquid chromatography over silica gel ((I) eluent: CH2Cl2/CH3OH 96/4; (II) eluent: CH2Cl2/CH3OH 97.5/2.5). The desired fractions were collected and the solvent was evaporated. The residue was repurified by high-performance liquid chromatography over Kromasil C18 (eluent: CH3OH/H2O 70/30). The desired fractions were collected and the solvent was evaporated. The residue was crystallized from Et2O/hexane, filtered off and dried, yielding 0.113 g (6%) of (±)-N-[4-cyanomethoxyphenylmethyl)phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide. (compound 76)

Workup

  1. temperaturerefluxed for 30 minutes
  2. customThe solvent was evaporated
  3. customThe residue was purified by high-performance liquid chromatography over silica gel ((I) eluent: CH2Cl2/CH3OH 96/4; (II) eluent: CH2Cl2/CH3OH 97.5/2.5)
  4. customThe desired fractions were collected
  5. customthe solvent was evaporated
  6. customThe residue was repurified by high-performance liquid chromatography over Kromasil
  7. customThe desired fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from Et2O/hexane
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-67b746d3cb7044f6a16c37d0b303e159
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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