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Hydrochloric Acid → HCID 178440632、化合物

HRID 2048559
ノート
印刷プレビュー

反応式

HRID 2048559 の反応式
[CH2:1]([C:5]1[N:10]2[N:11]=[CH:12][CH:13]=[C:9]2[N:8]([CH:14]2[CH2:23][CH2:22][C:17]3(OCC[O:18]3)[CH2:16][CH2:15]2)[C:7](=[O:24])[C:6]=1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:28][CH:27]=1)[CH2:2][CH2:3][CH3:4].Cl.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([C:5]1[N:10]2[N:11]=[CH:12][CH:13]=[C:9]2[N:8]([C@H:14]2[CH2:23][CH2:22][C@H:17]([OH:18])[CH2:16][CH2:15]2)[C:7](=[O:24])[C:6]=1[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[C:33]([C:38]#[N:39])=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:30][CH:31]=1)[CH2:2][CH2:3][CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67008667HCID 67008667、化合物

生成物 1

HCID 178440632HCID 178440632、化合物収率 87.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

To a solution of 4′-{[7-butyl-4-(1,4-dioxaspiro[4.5]dec-8-yl)-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (3.6 g) in tetrahydrofuran (40 mL) was added 3M hydrochloric acid (40 mL), and the mixture was stirred at 70° C. for 2 hr. The mixture was allowed to cool, and diluted with ethyl acetate, and the mixture was neutralized with 8M aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was dissolved in ethanol (20 mL)-tetrahydrofuran (20 mL). Thereto was added sodium borohydride (0.26 g) at 0° C. After stirring for 1 hr, ethyl acetate and saturated aqueous ammonium chloride solution were added. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (2.9 g, 87%).

後処理

  1. temperatureto cool
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethanol (20 mL)-tetrahydrofuran (20 mL)
  7. additionThereto was added sodium borohydride (0.26 g) at 0° C
  8. stirringAfter stirring for 1 hr
  9. additionethyl acetate and saturated aqueous ammonium chloride solution were added
  10. extractionThe mixture was extracted with ethyl acetate
  11. washthe organic layer was washed with water and saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated
  14. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-685acb976ec54aa2abdc08b594b8451b
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592431B2

反応ノート

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