2-Methoxybenzaldehyde → 5-(Benzoxazol-2-yl)-2-(2-methoxyphenyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74306Notes

Reaction equation

HRID 74306 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].[CH:24](=O)[C:25]1[C:26]([O:31][CH3:32])=[CH:27][CH:28]=[CH:29][CH:30]=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:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])=[N:15][C:14]=2[CH:16]=1

Participants

6

Reactant 4

HCID 86582-MethoxybenzaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 674989905-(Benzoxazol-2-yl)-2-(2-methoxyphenyl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 82.4%

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) (150 mg, 0.485 mmol) in dimethylformamide (3 mL) was added o-anisaldehyde (79.2 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 (170 mg, 82% yield) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-6832d96523d74b14b53b384fc45388fb
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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