Dithiaoctanediol → (Z)-N-(2-Cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxamide

HRID 1478174

반응식

HRID 1478174 반응식
[CH:1]1([N:7]2[C:11](=[O:12])[C:10]([NH:13][C:14]([C:16]3[C:20]([CH3:21])=[C:19]([C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25])[O:18][N:17]=3)=[O:15])=[C:9]([CH3:28])[N:8]2[CH3:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(SCCO)CSCCO>CCOC(C)=O.[Pd]>[CH:1]1([N:7]2[C:11](=[O:12])[C:10]([NH:13][C:14]([C:16]3[C:20]([CH3:21])=[C:19](/[CH:22]=[CH:23]\[C:24]([CH3:26])([CH3:25])[CH3:27])[O:18][N:17]=3)=[O:15])=[C:9]([CH3:28])[N:8]2[CH3:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

5

반응물 2

HCID 78904DithiaoctanediolHCID 118511150N-(2-Cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxamide

생성물 1

HCID 118511121(Z)-N-(2-Cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxamide

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 8857Ethyl Acetate용매

실험 절차

N-(2-Cyclohexyl-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-5-(3,3-dimethylbut-1-yn-1-yl)-4-methylisoxazole-3-carboxamide (Example 7, Step 3)) (30 mg, 0.075 mmol) in EtOAc (3 mL) was treated with 2,2′-(ethane-1,2-diylbis(sulfanediyl))diethanol (13.72 mg, 0.075 mmol) and Pd-5% Barium sulphate (16.02 mg, 7.53 μmol). The mixture was degassed, thoroughly refilling with nitrogen and the mixture was stirred under an atmosphere of hydrogen at room temperature overnight. Further Pd-5% Barium sulphate (16.02 mg, 7.53 μmol) was added and the reaction mixture was stirred at room temperature under an atmosphere of hydrogen for 16 hours. The resulting mixture was filtered through Celite® eluting with EtOAc and the solvent was removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 0-100% EtOAc in iso-hexane afforded the title compound;

후처리

  1. customThe mixture was degassed
  2. stirringthe reaction mixture was stirred at room temperature under an atmosphere of hydrogen for 16 hours
  3. filtrationThe resulting mixture was filtered through Celite®
  4. washeluting with EtOAc
  5. customthe solvent was removed under reduced pressure
  6. customThe crude material was adsorbed onto silica and purification by chromatography
  7. washeluting with 0-100% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-e0eb9d9e3d6749e299366994d18a99ad
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403810B2

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