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

HRID 2354818Notes

Reaction equation

HRID 2354818 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-31b46f7e01bb40be8b319e03e9213fd6
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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