Propanal → N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(2-methoxyethyl)-N-propylamine

HRID 9201

反応式

HRID 9201 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]([CH2:23][CH3:24])[C:17]([NH:18][CH2:19][CH2:20][O:21][CH3:22])=[C:13]2[CH:12]=[CH:11][CH:10]=1.[CH:25](=O)[CH2:26][CH3:27].S(=O)(=O)(O)O.[BH4-].[Na+]>O1CCCC1.C(OCC)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]([CH2:23][CH3:24])[C:17]([N:18]([CH2:19][CH2:20][O:21][CH3:22])[CH2:25][CH2:26][CH3:27])=[C:13]2[CH:12]=[CH:11][CH:10]=1

参加物

8

反応物 4

HCID 527PropanalHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 21984623N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(2-methoxyethyl)amine

生成物 1

HCID 21984679N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(2-methoxyethyl)-N-propylamine

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(2-methoxyethyl)amine (14 mg) was dissolved in tetrahydrofuran (1 mL), and after adding propionaldehyde (0.016 mL) and 3 M aqueous sulfuric acid (0.77 mL), sodium borohydride (5.8 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 aqueous 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 (9.5 mg) as a light yellow oil.

後処理

  1. additionwas added in five portions
  2. stirringstirring
  3. washthe extract was washed with saturated aqueous sodium hydrogencarbonate and brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customthe residue was purified by preparative TLC [n-hexane:ethyl acetate (5:1), Rf=0.5]

出典と根拠

ORDレコード
ord-5add00d2fc5045eab00f8af0fde67517
出典データセット
uspto-grants-2006_08
特許番号
US07091215B2

関連ノート

読み込み中…