Acetic Anhydride → HCID 53630739, compound

HRID 655671Notes

Reaction equation

HRID 655671 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].C(N(CC)CC)C.[S:15]1[CH:19]=[CH:18][C:17]2[C:20]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][O:33][C:34]4[N:38]([CH3:39])[N:37]=[C:36]([NH2:40])[CH:35]=4)[CH2:26][CH2:25]3)=[CH:21][CH:22]=[CH:23][C:16]1=2.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[S:15]1[CH:19]=[CH:18][C:17]2[C:20]([N:24]3[CH2:25][CH2:26][N:27]([CH2:30][CH2:31][CH2:32][O:33][C:34]4[N:38]([CH3:39])[N:37]=[C:36]([NH:40][C:1](=[O:3])[CH3:2])[CH:35]=4)[CH2:28][CH2:29]3)=[CH:21][CH:22]=[CH:23][C:16]1=2

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 57499609HCID 57499609, compound

Product 1

HCID 53630739HCID 53630739, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (1 ml) and triethylamine (0.09 ml, 0.65 mmol) were added to a dichloromethane solution (4 ml) of 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazol-3-yl-amine (0.20 g, 0.54 mmol) and the mixture was stirred at room temperature for 6 hours. An aqueous potassium carbonate solution was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and thereafter concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=2:1→0:1). The purified product was concentrated under reduced pressure and the residue was recrystallized from a solvent mixture of ethyl acetate-diisopropylether to obtain N-{5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazol-3-yl}acetamide (0.19 g, 89% yield) as white powder.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=2:1→0:1)
  5. concentrationThe purified product was concentrated under reduced pressure
  6. customthe residue was recrystallized from a solvent mixture of ethyl acetate-diisopropylether

Sources & evidence

ORD record
ord-bf29a9e993e74097b8c0fc68ee438e8d
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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