Water → HCID 76587193, compound

HRID 1717398Notes

Reaction equation

HRID 1717398 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][CH:33]=1)[O:7][CH2:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)[N:12]=[N:11][C:10]=1[C:25]([NH:27][CH:28]1[CH2:30][CH2:29]1)=[O:26])(=O)[CH3:2].Cl.[NH2:35][OH:36].C([O-])(=O)C.[Na+].O>C(O)C>[CH:28]1([NH:27][C:25]([C:10]2[N:11]=[N:12][N:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=3)[C:9]=2[CH2:8][O:7][C:6]2[CH:31]=[CH:32][CH:33]=[C:4]([C:1](=[N:35][OH:36])[CH3:2])[CH:5]=2)=[O:26])[CH2:29][CH2:30]1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 57665225HCID 57665225, compound

Product 1

HCID 76587193HCID 76587193, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[(3-acetylphenoxy)methyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (100 mg) obtained in Example 489 in ethanol (4 ml) were added hydroxylamine hydrochloride (78 mg) and sodium acetate (92 mg), and the mixture was heated under reflux for 4 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to give the title compound as a colorless powder (88 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-304880eb15594bf2b0195a83a23ca3b2
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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