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

HRID 74189

Reaction equation

HRID 74189 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]([CH3:11])[CH3:16])=[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 498213835-(Benzoxazol-2-yl)-2-isopropyl-1-(tetrahydropyran-4-yl)benzimidazoleYield 80%

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), isopropyl aldehyde (0.04 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 (70 mg, 43.9% 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-41f1545eda4644bfabedeb1f49512b94
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

Loading…