Water → N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(3-hexyl)amine

HRID 9199Notes

Reaction equation

HRID 9199 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]([CH2:19][CH3:20])[C:17]([NH2:18])=[C:13]2[CH:12]=[CH:11][CH:10]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](O[C:38](=O)[CH3:39])OC(=O)C)(=O)C.[Na+].O>C(O)(=O)C.CCC(=O)CCC.C(OCC)(=O)C>[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]([CH2:19][CH3:20])[C:17]([NH:18][CH:2]([CH2:7][CH2:38][CH3:39])[CH2:3][CH3:4])=[C:13]2[CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 21984628[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]amine

Product 1

HCID 21984754N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(3-hexyl)amineYield 109.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 115093-HexanoneSolvent

Procedure

After dissolving [7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]amine (30 mg) in acetic acid (1 mL), 3-hexanone (0.024 mL) and sodium sulfate (139 mg) were added and the mixture was stirred at room temperature for 30 minutes. Sodium triacetoxyborohydride (41.5 mg) was then added, and stirring was continued for 2 hours. Water was added to the reaction mixture, extraction was performed with ethyl acetate and the extract was washed with saturated aqueous sodium hydrogencarbonate and brine. After drying the obtained organic layer over anhydrous magnesium sulfate and filtering it, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (21 mg) was obtained from the n-hexane:ethyl acetate (30:1) fraction as a yellow oil.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. washthe extract was washed with saturated aqueous sodium hydrogencarbonate and brine
  5. dry with materialAfter drying the obtained organic layer over anhydrous magnesium sulfate
  6. filtrationfiltering it
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff5644163a6b494b9ede73774b11d44a
Source dataset
uspto-grants-2006_08
Patent number
US07091215B2

Reaction notes

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