Potassium Carbonate → 5-(Benzoxazol-2-yl)-2-(3-chlorophenyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74308Notes

Reaction equation

HRID 74308 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].[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=O.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:28]([C:27]3[CH:30]=[CH:31][CH:32]=[C:25]([Cl:24])[CH:26]=3)=[N:15][C:14]=2[CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 114773-ChlorobenzaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 674983305-(Benzoxazol-2-yl)-2-(3-chlorophenyl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 94%

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) (150 mg, 0.485 mmol) in dimethylformamide (3 mL) was added m-chlorobenzaldehyde (81.8 mg, 0.582 mmol) and oxone (179 mg, 0.291 mmol), and this was stirred at room temperature for 2 hours. After the reaction was complete, aqueous potassium carbonate solution was added, and after this was filtered and washed with water, drying yielded the title compound (196 mg, 94% yield) as colorless crystals.

Workup

  1. filtrationafter this was filtered
  2. washwashed with water
  3. customdrying

Sources & evidence

ORD record
ord-37a267d7cd4d436ba00031ad94d19b84
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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