HCID 59351418, compound → HCID 59351345, compound

HRID 887417Notes

Reaction equation

HRID 887417 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]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:25]3[CH2:26][O:27][CH2:28][CH2:29][CH:30]=3)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]>CCOC(C)=O.[Pd].[O-2].[O-2].[Mn+4]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([CH:25]3[CH2:30][CH2:29][CH2:28][O:27][CH2:26]3)=[N:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

5

Reactant 1

HCID 59351418HCID 59351418, compound

Product 1

HCID 59351345HCID 59351345, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1H-Benzimidazol-2-yl(4-((3-(5,6-dihydro-2H-pyran-3-yl)-2-pyrazinyl)oxy)phenyl)methanone (0.20 g, 0.50 mmol) was suspended in 15 mL of EtOAc in a pressure tube. Palladium on carbon, 10% (0.20 g) was added. The mixture was hydrogenated at 50 psi. After 24 hours, the mixture was filtered through celite and eluted with 50 mL of 9:1 chloroform:isopropanol. The product was taken up in 10 mL of dichloromethane. Manganese dioxide (0.58 g, 6.7 mmol) was added. After 1 h, the mixture was filtered through celite and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (0 to 2% MeOH/dichloromethane) affording 1H-benzimidazol-2-yl(4-((3-(tetrahydro-2H-pyran-3-yl)-2-pyrazinyl)oxy)phenyl)methanone. MS (ESI, pos. ion) m/z: 401 (M+1). IC50 (uM) +++++.

Workup

  1. filtrationthe mixture was filtered through celite
  2. washeluted with 50 mL of 9:1 chloroform
  3. waitAfter 1 h
  4. filtrationthe mixture was filtered through celite and
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (0 to 2% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-f7ee6f797ab74766953459878f5ea167
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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