Acetic Acid → [7-(2-Chloro-4-methoxyphenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]amine

HRID 9198

反応式

HRID 9198 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]2[N:16]=[C:17]([CH2:22][CH3:23])[C:18]([N+:19]([O-])=O)=[C:14]2[CH:13]=[CH:12][CH:11]=1.O.C(O)(=O)C>C(O)C.[Zn]>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:15]2[N:16]=[C:17]([CH2:22][CH3:23])[C:18]([NH2:19])=[C:14]2[CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 219845837-(2-Chloro-4-methoxyphenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine

生成物 1

HCID 21984647[7-(2-Chloro-4-methoxyphenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]amine

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

7-(2-Chloro-4-methoxyphenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (5 mg) was suspended in ethanol (2 mL), and then water (1 mL), acetic acid (0.5 mL) and zinc powder (10 mg) were added and the mixture was heated and stirred at 80° C. for 30 minutes. The reaction mixture was filtered, water was added to the filtrate, extraction was performed with ethyl acetate and the extract was washed with saturated aqueous sodium hydrogencarbonate and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure to obtain [7-(2-chloro-4-methoxyphenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]amine as crude crystals. These were dissolved in tetrahydrofuran (1 mL) without further purification, and after adding propionaldehyde (0.015 mL) and 3 M aqueous sulfuric acid (0.071 mL), sodium borohydride (5.4 mg) was added in five portions while vigorously stirring on ice, and stirring was continued for 30 minutes. Water was added to the reaction mixture, extraction was performed with diethyl ether and the extract was washed with saturated sodium hydrogencarbonate and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure and the residue was purified by preparative TLC [n-hexane:ethyl acetate (5:1), Rf=0.5] to obtain the title compound (6 mg) as a light yellow oil.

後処理

  1. temperaturethe mixture was heated
  2. filtrationThe reaction mixture was filtered
  3. additionwater was added to the filtrate, extraction
  4. washthe extract was washed with saturated aqueous sodium hydrogencarbonate and brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  6. concentrationthe solvent was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-3ab709c49b514c698590f2525c78e682
出典データセット
uspto-grants-2006_08
特許番号
US07091215B2

関連ノート

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