Boron trifluoride etherate → HCID 46851172, compound

HRID 1913157Notes

Reaction equation

HRID 1913157 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24](=[NH:27])[NH:25][OH:26])=[CH:20][CH:19]=2)=[O:17])[CH2:12][CH2:11]1.[C:28](Cl)(=O)[CH2:29][CH3:30].B(F)(F)F.CCOCC>O1CCOCC1.C(Cl)Cl.C([O-])(O)=O.[Na+]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]3[N:27]=[C:28]([CH2:29][CH3:30])[O:26][N:25]=3)=[CH:22][CH:23]=2)=[O:17])[CH2:12][CH2:11]1

Participants

7

Reactant 3

HCID 8000Boron trifluoride etherateHCID 62324Propionyl chlorideHCID 178513317HCID 178513317, compound

Product 1

HCID 46851172HCID 46851172, compoundYield 3.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 4-{[4-(1H-benzimidazol-2-yl)piperidin-1-yl]carbonyl}-N-hydroxybenzene carboximidamide (0.15 g, 0.41 mmol) in anhydrous 1,4-dioxane (5 mL) is added dropwise propionyl chloride (34 μL, 0.39 mmol). The reaction is heated to 40° C. for 1 h before adding boron trifluoride etherate (10.5 μL, 0.083 mmol). Heating is continued at 80° C. for 4 h. The mixture is diluted with DCM and saturated aqueous NaHCO3 giving a suspension which is filtered. The organic layer is separated, dried over Na2SO4, filtered and concentrated under reduced pressure to give 5 mg of [4-(1H-benzimidazol-2-yl)piperidin-1-yl][4-(5-ethyl-1,2,4-oxadiazol-3-yl)phenyl]methanone.

Workup

  1. temperatureHeating
  2. filtrationis filtered
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26cd16a163df4f1daee281eb75ce6e44
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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