Pyridine → HCID 57499610, compound

HRID 655670Notes

Reaction equation

HRID 655670 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]4[N:24]([CH3:25])[N:23]=[C:22]([NH2:26])[CH:21]=4)[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2.C(N(CC)CC)C.[CH3:34][N:35]([CH3:39])[C:36]([Cl:38])=[O:37].N1C=CC=CC=1>O.ClCCl>[ClH:38].[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]4[N:24]([CH3:25])[N:23]=[C:22]([NH:26][C:36](=[O:37])[N:35]([CH3:39])[CH3:34])[CH:21]=4)[CH2:14][CH2:15]3)=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

7

Reactant 4

HCID 1049PyridineHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 57499609HCID 57499609, compound

Product 1

HCID 57499610HCID 57499610, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A dichloromethane solution (5 ml) of 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazol-3-yl-amine (0.27 g, 0.73 mmol) was cooled on ice. To this, triethylamine (0.36 ml, 2.5 mmol), dimethylcarbamoyl chloride (0.20 ml, 2.1 mmol) and pyridine (0.06 ml, 0.73 mmol) were added and the mixture was stirred at room temperature overnight. To the reaction solution, water was added and the reaction solution was 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=3:1→0:1). The purified product was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and a 4N-hydrochloride/ethyl acetate solution was added thereto. The crystal produced was filtrated and dried to obtain 3-{5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazol-3-yl}-1,1-dimethyl-urea hydrochloride (0.10 g, 30% yield), as light yellow powder.

Workup

  1. extractionthe reaction solution was 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=3:1→0:1)
  5. concentrationThe purified product was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. additiona 4N-hydrochloride/ethyl acetate solution was added
  8. customThe crystal produced
  9. filtrationwas filtrated
  10. customdried

Sources & evidence

ORD record
ord-609557c65a634447add889c23f66a777
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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