1,4-Dioxane → Jak3-IN-7

HRID 1912397ノート

反応式

HRID 1912397 の反応式
[CH3:1][CH:2]1[C:5]2([CH2:10][CH2:9][CH2:8][N:7]([C:11]3[C:12]4[CH:19]=[CH:18][NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH2:6]2)[NH:4][CH2:3]1.CC1N([C:26]([CH2:28][C:29]#[N:30])=[O:27])N=C(C)C=1.O1CCOCC1.C(=O)(O)[O-].[Na+]>O>[CH3:1][CH:2]1[C:5]2([CH2:10][CH2:9][CH2:8][N:7]([C:11]3[C:12]4[CH:19]=[CH:18][NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH2:6]2)[N:4]([C:26](=[O:27])[CH2:28][C:29]#[N:30])[CH2:3]1

参加物

6

反応物 4

HCID 312751,4-DioxaneHCID 2621013-(3,5-Dimethyl-1H-pyrazol-1-yl)-3-oxopropanenitrileHCID 516892Sodium BicarbonateHCID 582933114-(3-methyl-1,6-diazaspiro[3.5]non-6-yl)-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 50913620Jak3-IN-7収率 21.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

An optically-active compound of 4-(3-methyl-1,6-diazaspiro[3.5]non-6-yl)-7H-pyrrolo[2,3-d]pyrimidine (25 mg) was mixed with 1-cyanoacetyl-3,5-dimethylpyrazole (32 mg) and 1,4-dioxane (750 μl), and the mixture was stirred at 100° C. for 3.5 hours. The mixture was cooled to room temperature. Thereto were added water and saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The separated aqueous layer was extracted with ethyl acetate five times, and the combined organic layer was washed with water and concentrated under reduced pressure. The resulting residue was purified by silica-gel thin layer chromatography (eluent: chloroform/methanol=9/1). The resulting residue was purified by silica-gel thin layer chromatography (eluent: ethyl acetate/methanol=93/7) again. The resulting solid (8.0 mg) was slurry-washed with n-hexane/ethyl acetate solution to give the titled compound (6.7 mg).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe separated aqueous layer was extracted with ethyl acetate five times
  4. washthe combined organic layer was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica-gel thin layer chromatography (eluent: chloroform/methanol=9/1)
  7. customThe resulting residue was purified by silica-gel thin layer chromatography (eluent: ethyl acetate/methanol=93/7) again
  8. washThe resulting solid (8.0 mg) was slurry-washed with n-hexane/ethyl acetate solution

出典と根拠

ORDレコード
ord-bf60f4d017d84c879a65993acc105b20
出典データセット
uspto-grants-2013_12
特許番号
US08609647B2

反応ノート

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