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

HRID 74190

Reaction equation

HRID 74190 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].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)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:2]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:16]3)=[N:15][C:14]=2[CH:16]=1

Participants

6

Reactant 3

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

Product 1

HCID 498213845-(Benzoxazol-2-yl)-2-cyclohexyl-1-(tetrahydropyran-4-yl)benzimidazoleYield 119.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.15 g, 0.484 mmol) was dissolved in DMF (3 mL) and water (0.1 mL), cyclohexyl aldehyde (0.06 g, 0.561 mmol) was added followed by oxone (0.19 g, 0.310 mmol), and this was stirred at room temperature for 2.5 hours. Aqueous potassium carbonate solution (0.09 g/15 mL) was added to the reaction solution. This was extracted with chloroform, washed with water, and after drying over magnesium sulfate, this was concentrated and purified by silica gel column chromatography. The crystals obtained were washed with hexane and a small amount of ethyl acetate, and dried to yield the title compound (116 mg, 59.6% yield) as white crystals.

Workup

  1. extractionThis was extracted with chloroform
  2. washwashed with water
  3. dry with materialafter drying over magnesium sulfate
  4. concentrationthis was concentrated
  5. custompurified by silica gel column chromatography
  6. customThe crystals obtained
  7. washwere washed with hexane
  8. dry with materiala small amount of ethyl acetate, and dried

Sources & evidence

ORD record
ord-4e079b0582194ab0a4114a13fd2573db
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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