Diethylene Glycol Monomethyl Ether → 1-(4-Fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 2095805노트

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HRID 2095805 반응식
CO/[CH:3]=[CH:4]/[C:5](=O)[CH:6]([CH3:8])[CH3:7].[C:10]([CH2:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[O:14])#[N:11].N12CCN(CC1)CC2.COCCOCCO>C(OCC)(=O)C>[F:22][C:19]1[CH:18]=[CH:17][C:16]([N:15]2[C:5]([CH:6]([CH3:8])[CH3:7])=[CH:4][CH:3]=[C:12]([C:10]#[N:11])[C:13]2=[O:14])=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 8134Diethylene Glycol Monomethyl EtherHCID 9237DabcoHCID 6931482-Cyano-N-(4-fluorophenyl)acetamideHCID 18458636(1E)-1-methoxy-4-methylpent-1-en-3-one

생성물 1

HCID 669688061-(4-Fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile수율 59.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

A mixture of (1E)-1-methoxy-4-methylpenta-1-en-3-one (508 mg, 3.96 mmol), 2-cyano-N-(4-fluorophenyl)acetamide (847 mg, 4.75 mmol), 1,4-diazabicyclo[2.2.2]octane (444 mg, 3.96 mmol) and 2-(2-methoxyethoxy)ethanol (10 mL) was stirred at 130° C. for 6 hr. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with 1N hydrochloric acid, water (×2) and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→60/40) and silica gel column chromatography (NH silica gel, ethyl acetate/hexane=0/100→60/40) to give the title compound (604 mg, 59%) as a yellow solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with 1N hydrochloric acid, water (×2) and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→60/40) and silica gel column chromatography (NH silica gel, ethyl acetate/hexane=0/100→60/40)

출처 및 근거

ORD 기록
ord-8bb19a0d44b642d7a6cc67b29369b278
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445509B2

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