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Propanal → N-[7-(2,4-Dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]-N,N-dipropylamine

HRID 9211
Notes
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Reaction equation

HRID 9211 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]([S:22][CH3:23])[C:17]([NH:18][CH2:19][CH2:20][CH3:21])=[C:13]2[CH:12]=[CH:11][CH:10]=1.[CH:24](=O)[CH2:25][CH3:26].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]([S:22][CH3:23])[C:17]([N:18]([CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21])=[C:13]2[CH:12]=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 527PropanalHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 21984560N-[7-(2,4-Dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]-N-propylamine

Product 1

HCID 21984542N-[7-(2,4-Dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]-N,N-dipropylamine

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

N-[7-(2,4-dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]-N-propylamine (59 mg) was dissolved in tetrahydrofuran (1 mL), and after adding propionaldehyde (0.035 mL) and 3 M aqueous sulfuric acid (0.16 mL), sodium borohydride (12 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, the residue was purified by silica gel column chromatography, and the title compound (49 mg) was obtained from the n-hexane:ethyl acetate (100:1) fraction as a 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 silica gel column chromatography

Sources & evidence

ORD record
ord-37c8ee7b959f4025b20c8210680cbd20
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091215B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes