Triethylamine → 4-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}bicyclo[2.2.2]octane-1-carbohydrazide

HRID 2079835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079835
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])=[N:5][N:4]=[C:3]1[C:17]12[CH2:24][CH2:23][C:20]([C:25]([OH:27])=O)([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.F[P-](F)(F)(F)(F)F.CN(C)C=[N+](C)C.C(N(CC)CC)C.[NH2:49][NH2:50]>CN(C=O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])=[N:5][N:4]=[C:3]1[C:17]12[CH2:24][CH2:23][C:20]([C:25]([NH:49][NH2:50])=[O:27])([CH2:19][CH2:18]1)[CH2:21][CH2:22]2

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9321HydrazineHCID 592555694-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxylic acidHCID 866270241066-47-3

Produkt 1

HCID 592555674-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}bicyclo[2.2.2]octane-1-carbohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A portion of solid (4-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}bicyclo[2.2.2]octane-1-carboxylic acid 1-D (2.0 g, 5.27 mmol) was dissolved in anhydrous DMF (30 ml) and treated with N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (2.09 g, 7.91 mmol), triethyl amine (2.3 mL, 16.50 mmol), and hydrazine (0.50 mL, 15.93 mmol) at room temperature and a nitrogen atmosphere overnight. The solvent was removed in vacuo, and the residue was redissolved in methylene chloride (700 ml) and washed with saturated aqueous sodium bicarbonate, water, and brine. The product was dried over MgSO4 and the solvent removed to afford 13-A as a white powder. MS (ESI+)=394.13 (M+1).

Aufarbeitung

  1. customa nitrogen atmosphere overnight
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was redissolved in methylene chloride (700 ml)
  4. washwashed with saturated aqueous sodium bicarbonate, water, and brine
  5. dry with materialThe product was dried over MgSO4
  6. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-ccbff108381a480baa16135ef652ed25
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932280B2

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