Tributylphosphine → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-vinyl-1H-1,2,3-triazole-4-carboxamide

HRID 1717319Notes

Reaction equation

HRID 1717319 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=3)[C:11]=2[CH2:12][CH2:13]O)=[O:6])[CH2:3][CH2:2]1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=3)[C:11]=2[CH:12]=[CH2:13])=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57664851HCID 57664851, compound

Product 1

HCID 57664916N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-vinyl-1H-1,2,3-triazole-4-carboxamideYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(2-hydroxyethyl)-1H-1,2,3-triazole-4-carboxamide (124 mg, 0.361 mmol) obtained in Example 114 was dissolved in THF (2.5 ml), tributylphosphine (102 mg, 0.469 mmol, 1.3 eq.) and ADDP (120 mg, 0.469 mmol, 1.3 eq.) were added, and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was diluted with ethyl acetate (30 ml), washed with 2% aqueous sodium carbonate solution, 10% aqueous sodium chloride solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was subjected to column chromatography (elution solvent, ethyl acetate-hexane=1:1-2:1) on silica gel (manufactured by E. Merck, Art.7734, 10 g). The fraction obtained by elution with ethyl acetate-hexane (3:2-2:1) was concentrated, and diethyl ether was added. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (101 mg, 0.310 mmol, 86.0%).

Workup

  1. washwashed with 2% aqueous sodium carbonate solution, 10% aqueous sodium chloride solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. washThe residue was subjected to column chromatography (elution solvent, ethyl acetate-hexane=1:1-2:1) on silica gel (manufactured by E. Merck, Art.7734, 10 g)
  5. customThe fraction obtained by elution with ethyl acetate-hexane (3:2-2:1)
  6. concentrationwas concentrated
  7. additiondiethyl ether was added
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-e864e287daaf4ce88be4fdf8e50d0c99
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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