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

HRID 9201

반응식

HRID 9201 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-5add00d2fc5045eab00f8af0fde67517
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091215B2

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