Potassium Carbonate → 5-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)-2-(tetrahydropyran-4-yl)methylbenzimidazole

HRID 74292Notes

Reaction equation

HRID 74292 reaction equation
[O: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]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[O:24]1[CH2:29][CH2:28][CH:27]([CH2:30][CH:31]=O)[CH2:26][CH2:25]1.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O: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]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:31]([CH2:30][CH:27]3[CH2:28][CH2:29][O:24][CH2:25][CH2:26]3)=[N:15][C:14]=2[CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 177509432-(Oxan-4-yl)acetaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 674987895-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)-2-(tetrahydropyran-4-yl)methylbenzimidazoleYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (250 mg, 0.808 mmol) in dimethylformamide (3 mL) was added (4-tetrahydropyranyl)acetaldehyde (114 mg, 0.889 mmol) and oxone (323 mg, 0.525 mmol), and this was stirred at room temperature for 2 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (197 mg, 58% yield) as light brown crystals.

Workup

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4b009fd76b104329bfd0994f00e9425e
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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