Methanol → 1-(3,5-Difluorobenzyl)-5-[(4-methyl-1-piperazinyl)methyl]-2-mercaptoimidazole

HRID 1762803Notes

Reaction equation

HRID 1762803 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([F:24])[CH:23]=1)[CH2:5][N:6]1[C:10]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=O)=[CH:9][N:8]=[C:7]1[SH:20].B.CSC.CO>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([F:24])[CH:23]=1)[CH2:5][N:6]1[C:10]([CH2:11][N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:9][N:8]=[C:7]1[SH:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 178481054HCID 178481054, compound

Product 1

HCID 1784808401-(3,5-Difluorobenzyl)-5-[(4-methyl-1-piperazinyl)methyl]-2-mercaptoimidazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(3,5-difluorobenzyl)-5-[(4-methyl-1-piperazinyl)carbonyl]-2-mercaptoimidazole (1.37 g, 3.89 mmole) in chloroform (15 ml) was added dropwise 1 molar borane-methyl sulfide (23.3 ml, 23.3 mmole) and the solution was stirred for 4 hours at 25° C. The reaction mixture was cooled in ice and methyl alcohol was added dropwise until gas evolution ceased. The solvent was removed by evaporation at reduced pressure, ten portions of methyl alcohol were added, the reaction mixture was heated at reflux for 5 minutes and the solvent was removed at reduced pressure. The crude product was dissolved in methylene chloride-methanol (9:1) and purified by flash slica chromatography. The product was purified by trituration with ethyl acetate and recrystallization from ethanol to give 1-(3,5-difluorobenzyl)-5-[(4-methyl-1-piperazinyl)methyl]-2-mercaptoimidazole as a solid, m.p.: 200°-201° C. (0.820 g, 62%).

Workup

  1. temperatureThe reaction mixture was cooled in ice
  2. customThe solvent was removed by evaporation at reduced pressure, ten portions of methyl alcohol
  3. additionwere added
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 5 minutes
  6. customthe solvent was removed at reduced pressure
  7. dissolutionThe crude product was dissolved in methylene chloride-methanol (9:1)
  8. custompurified by flash slica chromatography
  9. customThe product was purified by trituration with ethyl acetate and recrystallization from ethanol

Sources & evidence

ORD record
ord-dd352ff46c8c4f92a88c1450d6fdb9f0
Source dataset
uspto-grants-1989_05
Patent number
US04835154

Reaction notes

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