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

HRID 9201

Reaction equation

HRID 9201 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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]

Sources & evidence

ORD record
ord-5add00d2fc5045eab00f8af0fde67517
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Linked notes

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