Water → 5-(Benzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)-6-chlorobenzimidazole

HRID 74296Notes

Reaction equation

HRID 74296 reaction equation
[Cl:1][C:2]1[C:8]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:7][C:5]([NH2:6])=[C:4]([NH:18][CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:3]=1.Cl.[C:26](=N)(OC)[CH3:27].O>CO>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:8]1[C:2]([Cl:1])=[CH:3][C:4]2[N:18]([CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:26]([CH3:27])=[N:6][C:5]=2[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 67498666HCID 67498666, compound

Product 1

HCID 674990465-(Benzoxazol-2-yl)-2-methyl-1-(tetrahydropyran-4-yl)-6-chlorobenzimidazoleYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-chloro-2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 112-3) (0.04 g, 0.2 mmol) in methanol (1.2 mL) was added methyl acetimidate hydrochloride (0.06 g, 0.6 mmol), and this was heated to reflux for 3 hours. After the reaction solution was cooled, water was added, and the precipitated crystals were filtered, and after being washed with water were dried to yield the title compound (0.03 g, 79% yield) as a yellowish-brown solid.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter the reaction solution was cooled
  4. filtrationthe precipitated crystals were filtered
  5. washafter being washed with water
  6. customwere dried

Sources & evidence

ORD record
ord-64fdf773b4be4b79bf36b465f00207e1
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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