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

HRID 2424616노트

반응식

HRID 2424616 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ae7861b83cd843b7920a587d5d642a6b
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964591B2

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