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1,1'-Carbonyldiimidazole → 4-{-4-Methyl-5-[2-(trifluoromethyl)phenyl]-4h-1,2,4-triazol-3-yl}-n'-(4,4,4-trifluoro-2-methylbutanoyl)bicyclo[2.2.2]octane-1-carbohydrazide

HRID 2079836
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Reaktionsgleichung

Reaktionsgleichung von HRID 2079836
[CH3:1][CH:2]([CH2:6][C:7]([F:10])([F:9])[F:8])[C:3](O)=[O:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:23][N:24]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([F:38])([F:37])[F:36])=[N:27][N:26]=[C:25]1[C:39]12[CH2:46][CH2:45][C:42]([C:47]([NH:49][NH2:50])=[O:48])([CH2:43][CH2:44]1)[CH2:41][CH2:40]2>CN(C=O)C>[CH3:23][N:24]1[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([F:36])([F:38])[F:37])=[N:27][N:26]=[C:25]1[C:39]12[CH2:46][CH2:45][C:42]([C:47]([NH:49][NH:50][C:3](=[O:4])[CH:2]([CH3:1])[CH2:6][C:7]([F:10])([F:9])[F:8])=[O:48])([CH2:41][CH2:40]1)[CH2:43][CH2:44]2
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Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27755364,4,4-Trifluoro-2-methylbutanoic acidHCID 592555674-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}bicyclo[2.2.2]octane-1-carbohydrazide

Produkt 1

HCID 575723784-{-4-Methyl-5-[2-(trifluoromethyl)phenyl]-4h-1,2,4-triazol-3-yl}-n'-(4,4,4-trifluoro-2-methylbutanoyl)bicyclo[2.2.2]octane-1-carbohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-methyl-4,4,4-trifluorobutyric acid (108 mg, 0.692 mmol) and 1,1′-carbonyldiimidazole (101 mg, 0.623 mmol) in DMF (1 ml) was stirred at room temperature under a nitrogen atmosphere. After 30 min, compound 13-A (100 mg, 0.254 mmol) was added and the solution stirred overnight. DMF was removed in vacuo and the solid was redissolved in CH3CN (4 ml). Product was purified by Gilson reverse phase chromatography eluting with a 10-90% CH3CN (0.1% TFA)/water (0.1% TFA) gradient. Solvent was removed in vacuo and the product free based from methylene chloride and saturated aqueous sodium bicarbonate. The organic layer was dried over MgSO4 and the solvent removed to yield 13-B as a white solid. MS (ESI+)=532.18 (M+1).

Aufarbeitung

  1. customDMF was removed in vacuo
  2. dissolutionthe solid was redissolved in CH3CN (4 ml)
  3. customProduct was purified by Gilson reverse phase chromatography
  4. washeluting with a 10-90% CH3CN (0.1% TFA)/water (0.1% TFA) gradient
  5. customSolvent was removed in vacuo
  6. dry with materialThe organic layer was dried over MgSO4
  7. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-5c819015ada648fcb35fe7c0c7c03089
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07932280B2

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