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

HRID 2095805ノート

反応式

HRID 2095805 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8bb19a0d44b642d7a6cc67b29369b278
出典データセット
uspto-grants-2013_05
特許番号
US08445509B2

反応ノート

読み込み中…