Potassium Carbonate → 2-(4-Acetylaminophenyl)-5-(5-chlorobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74284

Reaction equation

HRID 74284 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.[CH3:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]=O)=[CH:31][CH:30]=1)=[O:27].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:17]([CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:13]3[CH:12]=[CH:11][C:10]([C:8]4[O:9][C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:24][C:6]=5[N:7]=4)=[CH:16][C:14]=3[N:15]=2)=[CH:31][CH:30]=1)(=[O:27])[CH3:25]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 739424-AcetamidobenzaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 674984215-Chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674980792-(4-Acetylaminophenyl)-5-(5-chlorobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 74%

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 4-formylacetanilide (142 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 washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (261 mg, 74% yield) as white crystals.

Workup

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b36a7d30a2134c15bb82b48512952a80
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

Loading…