HCID 68670051, compound → HCID 68670179, compound

HRID 2047371Notes

Reaction equation

HRID 2047371 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[C:12]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([CH:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)=O)[CH2:18][CH2:17]2)[CH:13]=[CH:14][CH:15]=1>C1COCC1>[CH3:30][N:27]1[CH2:26][CH2:25][CH:24]([CH2:22][N:19]2[CH2:20][CH2:21][N:16]([C:12]3[CH:11]=[C:10]([C:2]4[NH:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)[CH:15]=[CH:14][CH:13]=3)[CH2:17][CH2:18]2)[CH2:29][CH2:28]1

Participants

3

Reactant 1

HCID 68670051HCID 68670051, compound

Product 1

HCID 68670179HCID 68670179, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of {4-[3-(1H-benzoimidazol-2-yl)-phenyl]-piperazin-1-yl}-(1-methyl-piperidin-4-yl)-methanone (0.12 g, 0.35 mmol) in dry THF (4 mL) boran-methyl sulfide complex in THF ((CH3)2S.BH3) (0.07 mL, 0.74 mmol) was added and the resulting suspension was heated at 60° C. overnight. The reaction was then cooled to room temperature, the solvent removed under reduced pressure and 1N HCl (3 mL) was added to the residue before heating at 100° C. for 5 h. The reaction was then cooled to room temperature, neutralized with 10% NaOH and extracted with dichloromethane (3×10 mL) The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a residue that was purified by Preparative HPLC, to obtain 0.08 g (69%) of the title compound.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customthe solvent removed under reduced pressure and 1N HCl (3 mL)
  3. additionwas added to the residue
  4. temperaturebefore heating at 100° C. for 5 h
  5. temperatureThe reaction was then cooled to room temperature
  6. extractionextracted with dichloromethane (3×10 mL) The combined organic layers
  7. dry with materialwere dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a residue that
  11. customwas purified by Preparative HPLC

Sources & evidence

ORD record
ord-0846781953cf4675a887daa070efe760
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

Loading…