Triethylamine → 8-(1-(4-Methoxyphenyl)-5-(6-methylpyridin-3-yl)-1H-pyrazol-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1802523ノート

反応式

HRID 1802523 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.C(N(CC)CC)C.[OH:19][C:20]1([C:30]#[C:31][C:32]([C:34]2[CH:35]=[N:36][C:37]([CH3:40])=[CH:38][CH:39]=2)=O)[CH2:29][CH2:28][C:23]2([O:27][CH2:26][CH2:25][O:24]2)[CH2:22][CH2:21]1>C(O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:32]([C:34]3[CH:35]=[N:36][C:37]([CH3:40])=[CH:38][CH:39]=3)=[CH:31][C:30]([C:20]3([OH:19])[CH2:21][CH2:22][C:23]4([O:27][CH2:26][CH2:25][O:24]4)[CH2:28][CH2:29]3)=[N:11]2)=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 583993863-(8-Hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-1-(6-methylpyridin-3-yl)-2-propyn-1-one

生成物 1

HCID 672963498-(1-(4-Methoxyphenyl)-5-(6-methylpyridin-3-yl)-1H-pyrazol-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol収率 22.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a solution of 4-methoxyphenylhydrazine hydrochloride (359 mg, 2.06 mmol) in ethanol (4 mL), triethylamine (286 μL, 2.06 mmol) was added dropwise, and the obtained solution was stirred at room temperature for 30 minutes. To the reaction solution, a solution of 3-(8-hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-1-(6-methylpyridin-3-yl)-2-propyn-1-one (Reference Example 16) (563.7 mg, 1.87 mmol) in ethanol (5.4 mL) was added dropwise, and the obtained solution was stirred at room temperature for 22 hours. Thereafter, the reaction solution was concentrated under reduced pressure. Water was added to the residue and the resultant was extracted with ethyl acetate. The organic layer was washed with distilled water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (177 mg, 0.42 mmol, 22%) as an amorphous product.

後処理

  1. stirringthe obtained solution was stirred at room temperature for 22 hours
  2. concentrationThereafter, the reaction solution was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe resultant was extracted with ethyl acetate
  5. washThe organic layer was washed with distilled water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-c57e6b4820d448e8b41f4e6c0c3c6d32
出典データセット
uspto-grants-2013_01
特許番号
US08349874B2

反応ノート

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