Sodium Bicarbonate → 1-[1-(3-Chloro-2-pyridyl)-5-methyl-4-pyrazolyl]-3-[4-(3,5-difluorophenyl)-1-piperazinyl]-1-trans-propene Hydrochloride

HRID 1267082Notes

Reaction equation

HRID 1267082 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][N:7]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[C:8]=1[CH3:9])(=O)[CH3:2].[F:17][C:18]1[CH:19]=[C:20]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:21]=[C:22]([F:24])[CH:23]=1.Cl.[CH2:32](O)C.C(=O)([O-])O.[Na+]>C(O)C>[ClH:16].[Cl:16][C:15]1[C:10]([N:7]2[C:8]([CH3:9])=[C:4](/[CH:1]=[CH:2]/[CH2:32][N:28]3[CH2:29][CH2:30][N:25]([C:20]4[CH:19]=[C:18]([F:17])[CH:23]=[C:22]([F:24])[CH:21]=4)[CH2:26][CH2:27]3)[CH:5]=[N:6]2)=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 109872191-(3,5-Difluorophenyl)piperazineHCID 118172064-Acetyl-1-(3-chloro-2-pyridyl)-5-methylpyrazoleHCID 21887872Ethanol hydrochloride

Product 1

HCID 185452931-[1-(3-Chloro-2-pyridyl)-5-methyl-4-pyrazolyl]-3-[4-(3,5-difluorophenyl)-1-piperazinyl]-1-trans-propene Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 40 ml of absolute ethanol was dissolved 0.72 g of 4-acetyl-1-(3-chloro-2-pyridyl)-5-methylpyrazole, and 1.38 g of 1-(3,5-difluorophenyl)piperazine, 7 ml of a 1N hydrochloric acid/ethanol solution, and 0.917 g of p-formaldehyde were added thereto, followed by refluxing for 20 hours. To the reaction mixture was further added 0.917 g of p-formaldehyde, followed by refluxing for 50 hours. After the reaction mixture was allowed to stand at room temperature for 21 hours, a saturated aqeous solution of sodium hydrogencarbonate was added thereto, and the mixture was extracted with chloroform three times. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation. The residue was subjected to silica gel column chromatography using a mixture of chloroform-methanol (50:1 by volume) as a developing solvent. The fraction containing the desired compound was concentrated to yield 0.72 g of the title compound.

Workup

  1. additionwere added
  2. temperatureby refluxing for 20 hours
  3. temperatureby refluxing for 50 hours
  4. extractionthe mixture was extracted with chloroform three times
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation
  7. additiona mixture of chloroform-methanol (50:1 by volume) as a developing solvent
  8. additionThe fraction containing the desired compound
  9. concentrationwas concentrated

Sources & evidence

ORD record
ord-67de3da8c3a64c8cab544c1c7abf8956
Source dataset
uspto-grants-2003_04
Patent number
US06552018B1

Reaction notes

Loading…