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

HRID 1717319ノート

反応式

HRID 1717319 の反応式
[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

参加物

6

反応物 3

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57664851HCID 57664851、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e864e287daaf4ce88be4fdf8e50d0c99
出典データセット
uspto-grants-2010_09
特許番号
US07803822B2

反応ノート

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