Triacetoxyperiodinane → 6-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYL-2-OXOETHYL)AMIDE

HRID 2056606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2056606
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([CH:26]([OH:55])[CH2:27][NH:28][C:29]([C:31]2[N:32]=[N:33][C:34]([N:37]3[CH2:42][CH2:41][N:40]([C:43](=[O:54])[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=4[C:50]([F:53])([F:52])[F:51])[CH2:39][CH2:38]3)=[CH:35][CH:36]=2)=[O:30])[CH2:25][CH2:24]1>C(OCC)(=O)C>[CH:23]1([C:26](=[O:55])[CH2:27][NH:28][C:29]([C:31]2[N:32]=[N:33][C:34]([N:37]3[CH2:38][CH2:39][N:40]([C:43](=[O:54])[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=4[C:50]([F:53])([F:52])[F:51])[CH2:41][CH2:42]3)=[CH:35][CH:36]=2)=[O:30])[CH2:25][CH2:24]1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 11751599N-(2-cyclopropyl-2-hydroxyethyl)-6-(4-(2-(trifluoromethyl)benzoyl)piperazin-1-yl)pyridazine-3-carboxamide

Produkt 1

HCID 670125566-[4-(2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (2-CYCLOPROPYL-2-OXOETHYL)AMIDEAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dess-Martin periodinane (0.55 g, 1.3 mmol) was added to a solution of 6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-cyclopropyl-2-hydroxyethyl)amide (0.50 g, 1.07 mmol), the resulting reaction mixture was stirred at ambient temperature for 2 h, then diluted with ethyl acetate, sequentially washed with 10% Na2S2O3 solution, saturated NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography and recrystallized from ethyl acetate-hexanes to give the title compound in 87% yield (0.43 g). 1H NMR (300 MHz, CDCl3) δ 8.45-8.41, 8.02, 7.72, 7.63-7.51, 7.34, 7.00, 4.48, 4.47-3.28, 2.00-1.94, 1.18-1.11, 1.10-0.82. 13C NMR (75 MHz, CDCl3) δ 204.4, 167.6, 163.1, 159.8, 144.9, 134.2, 132.3, 129.5, 129.0, 127.5, 127.2, 126.9, 121.8, 118.1, 112.4, 49.5, 46.3, 44.6, 44.4, 41.2, 18.7, 11.4. MS (ES+) m/z 462.0 (M+1).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. washsequentially washed with 10% Na2S2O3 solution, saturated NaHCO3 and brine
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. customrecrystallized from ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7259563388a54c5d97209a8b6eb37082
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335658B2

Notizen zur Reaktion

Wird geladen…