Potassium Carbonate → 5-(5-Chlorobenzoxazol-2-yl)-2-(4-methoxycarbonylphenyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74285Notes

Reaction equation

HRID 74285 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[C:14]([CH:16]=3)[NH2:15])=[N:7][C:6]=2[CH:24]=1.[CH:25]([C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1)=O.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]4[N:17]([CH:18]5[CH2:19][CH2:20][O:21][CH2:22][CH2:23]5)[C:25]([C:27]5[CH:28]=[CH:29][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:35][CH:36]=5)=[N:15][C:14]=4[CH:16]=3)=[N:7][C:6]=2[CH:24]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 15294Methyl 4-FormylbenzoateHCID 23707502Potassium hydroxy sulfiteHCID 674984215-Chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 498214605-(5-Chlorobenzoxazol-2-yl)-2-(4-methoxycarbonylphenyl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 100-2) (250 mg, 0.727 mmol) in dimethylformamide (3 mL) was added methyl 4-formylbenzoate (143 mg, 0.872 mmol) and oxone (313 mg, 0.509 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 after washing with water and ethyl acetate, drying yield the title compound (239 mg, 67% yield) as pale yellow crystals.

Workup

  1. filtrationthis was filtered
  2. washafter washing with water and ethyl acetate
  3. customdrying

Sources & evidence

ORD record
ord-98680170c5cf4f7e8c6e0fc5a75d7254
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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