Water → 5-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)-2-trichloromethylbenzimidazole

HRID 74249Notes

Reaction equation

HRID 74249 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.[Cl:25][C:26]([Cl:32])([Cl:31])[C:27](=N)OC.O>C(O)(=O)C>[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:27]([C:26]([Cl:32])([Cl:31])[Cl:25])=[N:15][C:14]=2[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoanilineHCID 86664949HCID 86664949, compound

Product 1

HCID 674979175-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)-2-trichloromethylbenzimidazoleYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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 acetic acid (3 mL) was added methyl 2,2,2-trichloroacetimidate hydrochloride (94.1 mg, 0.533 mmol), and this was stirred at room temperature for 4 hours. After the reaction was complete, water was added, and the precipitated crystals were filtered, and after being washed with water were dried to yield the title compound (196 mg, 93% yield) as gray crystals.

Workup

  1. filtrationthe precipitated crystals were filtered
  2. washafter being washed with water
  3. customwere dried

Sources & evidence

ORD record
ord-97e654b488ac4c1e92c727dcf11b99c9
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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