Water → HCID 178429394, compound

HRID 1458985Notes

Reaction equation

HRID 1458985 reaction equation
B(Br)(Br)Br.[ClH:5].[CH3:6][C:7]1[N:11]([C:12]2[N:17]=[C:16]([O:18]C)[CH:15]=[C:14]([CH3:20])[N:13]=2)[N:10]=[CH:9][C:8]=1[C:21](=[O:37])[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:26][CH2:25]1.O>C(Cl)Cl>[ClH:5].[CH3:6][C:7]1[N:11]([C:12]2[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([CH3:20])[N:13]=2)[N:10]=[CH:9][C:8]=1[C:21](=[O:37])[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22097308HCID 22097308, compound

Product 1

HCID 178429394HCID 178429394, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

300 mg of boron tribromide was added to 3 ml of methylene chloride and the obtained solution was cooled. Into the solution was dropped a solution of 470 mg of 1-[5-methyl-1-(4-methoxy-6-methyl-2-pyrimidinyl)-4-pyrazolyl]-3-[4-(2-methylphenyl)-1-piperazinyl]-1-propanone hydrochloride in 100 ml of methylene chloride. After stirring at room temperature for 72 hours, water was added and the mixture was extracted with methylene chloride twice. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (silica gel 800 g, chloroform:methanol=10:1-5:1). Then the obtained product was converted into hydrochloride by adding a 1N hydrochloric acid/ethanol solution and recrystallized from ethanol to thereby give 150 mg of the title compound.

Workup

  1. temperaturethe obtained solution was cooled
  2. extractionthe mixture was extracted with methylene chloride twice
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  5. customAfter evaporating the solvent
  6. customthe residue was purified by silica gel column chromatography (silica gel 800 g, chloroform:methanol=10:1-5:1)
  7. additionby adding a 1N hydrochloric acid/ethanol solution
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1379573a4ccb4bcbb7ead48e5e51d172
Source dataset
uspto-grants-1998_12
Patent number
US05852019

Reaction notes

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