Sodium Hydroxide → N-[7-(2,4-Dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]-N-propylamine

HRID 9210

反応式

HRID 9210 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([S:26][CH3:27])[C:17]([NH:18][C:19](=O)OC(C)(C)C)=[C:13]2[CH:12]=[CH:11][CH:10]=1.[H-].[Na+].I[CH2:31][CH2:32]C.Cl.C(OCC)(=O)C.[OH-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([S:26][CH3:27])[C:17]([NH:18][CH2:19][CH2:31][CH3:32])=[C:13]2[CH:12]=[CH:11][CH:10]=1

参加物

9

反応物 5

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 21866389Hydrogen chloride-ethyl acetateHCID 21984611tert-butyl N-[7-(2,4-dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate

生成物 1

HCID 21984560N-[7-(2,4-Dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]-N-propylamine

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

After dissolving tert-butyl N-[7-(2,4-dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate (150 mg) in N,N-dimethylformamide (3 mL), sodium hydride (60%, 21 mg) was added while cooling on ice, and then 1-iodopropane (0.041 mL) was added and the mixture was stirred for 30 minutes. Water was added to the reaction mixture, extraction was performed with ethyl acetate and the extract was washed with brine. The obtained organic layer was dried over anhydrous magnesium sulfate and filtered, and then the solvent was distilled off under reduced pressure to obtain a crude product. This was dissolved in ethyl acetate (1 mL) without purification, a 4 N hydrochloric acid/ethyl acetate solution (4 mL) was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was neutralized with 5 N aqueous sodium hydroxide while cooling on ice, and then extraction was performed with ethyl acetate and the organic layer was washed with water and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (60 mg) was obtained from the n-hexane:ethyl acetate (20:1) fraction as a yellow oil.

後処理

  1. additionwas added
  2. temperaturewhile cooling on ice
  3. washthe extract was washed with brine
  4. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a crude product
  8. stirringthe mixture was stirred at room temperature for 2 hours
  9. temperaturewhile cooling on ice
  10. extractionextraction
  11. washthe organic layer was washed with water and brine
  12. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  13. concentrationthe solvent was concentrated under reduced pressure
  14. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d6d9ef502a3f4df18fbb4eeb81fb5ea4
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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