Acetaldehyde → 2-Methyl-5-(4-methylbenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74215Notes

Reaction equation

HRID 74215 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]3[O:16][C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:11][C:9]=2[NH2:10])[CH2:3][CH2:2]1.[CH:24](=O)[CH3:25].OOS([O-])=O.[K+].[C:33](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:24][C:25]1[N:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[C:8]2[CH:14]=[CH:13][C:12]([C:15]3[O:16][C:17]4[CH:23]=[CH:22][CH:21]=[C:20]([CH3:33])[C:18]=4[N:19]=3)=[CH:11][C:9]=2[N:10]=1

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 674988722-Methyl-5-(4-methylbenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 20.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 46-2) (0.56 g, 1.7 mmol) in dimethylformamide (5 mL) containing water (0.18 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 90 mg, 1.8 mmol) and oxone (0.69 mg, 1.1 mmol), and this was stirred at room temperature for 3 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 (123 mg, 20.4% yield) as light brown 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-764065c8d4984caeb5f455023038785f
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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