Water → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(1E)-2-phenylprop-1-en-1-yl]-1H-1,2,3-triazole-4-carboxamide

HRID 1717382Notes

Reaction equation

HRID 1717382 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=3)[C:11]=2[CH2:12]P(OCC)(OCC)=O)=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].[C:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=O)[CH3:35].O>C1COCC1>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=3)[C:11]=2/[CH:12]=[C:34](/[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)\[CH3:35])=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 7410AcetophenoneHCID 24758Sodium hydrideHCID 86629812N-cyclopropyl-5-(diethylphosphonomethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 57664737N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(1E)-2-phenylprop-1-en-1-yl]-1H-1,2,3-triazole-4-carboxamideYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of N-cyclopropyl-5-(diethylphosphonomethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (450 mg, 1.00 mmol) obtained in Example 321b) in THF (5 ml) was added sodium hydride (50% oil dispersion, 75 mg) at 0° C., and the mixture was stirred at room temperature for 1 hr. A solution of acetophenone (117 μl) in THF (5 ml) was added to the obtained reaction mixture, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was stirred at 60° C. for 15 hr and cooled to 0° C. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/4 to ethyl acetate) and recrystallized from ethyl acetate-hexane to give the title compound as a colorless powder (150 mg, 36%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. stirringThe reaction mixture was stirred at 60° C. for 15 hr
  3. temperaturecooled to 0° C
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/4 to ethyl acetate)
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-87088d2f3ca74bc1bce633e1d1316f40
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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