1H-1,2,4-Triazole → 1-({3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-5-yl}methyl)-1H-1,2,4-triazole

HRID 2221843노트

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HRID 2221843 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:36])=[C:9]([CH2:11][O:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][O:18][C:19]3[CH:23]=[C:22]([CH2:24]O)[N:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:20]=3)=[CH:15][C:14]=2[O:34][CH3:35])[N:10]=1.C(P(CCCC)CCCC)CCC.[NH:50]1[CH:54]=[N:53][CH:52]=[N:51]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C(OCC)(=O)C.O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:36])=[C:9]([CH2:11][O:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][O:18][C:19]3[CH:23]=[C:22]([CH2:24][N:50]4[CH:54]=[N:53][CH:52]=[N:51]4)[N:21]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:20]=3)=[CH:15][C:14]=2[O:34][CH3:35])[N:10]=1

참가 물질

7

반응물 4

HCID 92571H-1,2,4-TriazoleHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 69218567HCID 69218567, 화합물

생성물 1

HCID 692151011-({3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-5-yl}methyl)-1H-1,2,4-triazole수율 85.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of {3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-5-yl}methanol (0.50 g), tributylphosphine (0.61 g), 1H-1,2,4-triazole (0.21 g) and tetrahydrofuran (80 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.75 g) at room temperature, and the mixture was stirred for 15 hrs. Ethyl acetate was added to the reaction mixture. The ethyl acetate layer was washed successively with 1N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 1-({3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-5-yl}methyl)-1H-1,2,4-triazole as crystals (0.47 g, yield 85%) from a fraction eluted with ethyl acetate-hexane (2:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 95-96° C.

후처리

  1. washThe ethyl acetate layer was washed successively with 1N hydrochloric acid and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cd5decd52c8640489ff9b1524877e95e
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368578B2

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