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Thionyl Chloride → 2-(4-{4-Methyl-5-[2-(trifluoromethyl)phenyl]-4h-1,2,4-triazol-3-yl}bicyclo[2.2.2]oct-1-yl)-5-(3,3,3-trifluoro-1-methylpropyl)-1,3,4-oxadiazole

HRID 2079837
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2079837
[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:27][NH:28][C:29](=[O:37])[CH:30]([CH3:36])[CH2:31][C:32]([F:35])([F:34])[F:33])=O)([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.S(Cl)(Cl)=O>C1(C)C=CC=CC=1.CC#N>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:14])([F:16])[F:15])=[N:5][N:4]=[C:3]1[C:17]12[CH2:24][CH2:23][C:20]([C:25]3[O:37][C:29]([CH:30]([CH3:36])[CH2:31][C:32]([F:34])([F:35])[F:33])=[N:28][N:27]=3)([CH2:21][CH2:22]1)[CH2:19][CH2:18]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 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

Produkt 1

HCID 575723742-(4-{4-Methyl-5-[2-(trifluoromethyl)phenyl]-4h-1,2,4-triazol-3-yl}bicyclo[2.2.2]oct-1-yl)-5-(3,3,3-trifluoro-1-methylpropyl)-1,3,4-oxadiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140Toluene
Lösungsmittel
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To 13-B in toluene (3 mL) was added thionyl chloride (2 mL) and, fitted with a reflux condenser, the solution was heated to 85° C. under a nitrogen atmosphere. After 1 hour the solvent was stripped off in vacuo. The residue was dissolved in CH3CN (4 ml) and product was purified by Masslynx 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 washed with brine and dried over MgSO4. The solvent was removed and the product lyopholyzed from CH3CN and water to afford 13-C as a white solid. MS (ESI+)=514.22 (M+1); 1H NMR (500 MHz, CDCl3): δ 7.85-7.83 (m, 1 H), 7.72-7.68 (m, 2 H), 7.52 (t, 1 H), 3.48 (s, 3 H), 3.46 (m, 1 H), 2.86-2.74 (m, 1 H), 2.51-2.39 (m, 1 H), 2.28 (m, 6 H), 2.14 (m, 6 H), 1.50 (d, 3 H) ppm.

Aufarbeitung

  1. customfitted with a reflux condenser
  2. customproduct was purified by Masslynx reverse phase chromatography
  3. washeluting with a 10-90% CH3CN (0.1% TFA)/water (0.1% TFA) gradient
  4. customSolvent was removed in vacuo
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-c9fd1cbf89004fd79765ea7977e82f70
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07932280B2

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