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

HRID 74287Notes

Reaction equation

HRID 74287 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.Cl.[C:26]([NH:29][CH2:30][C:31](=N)OCC)(=[O:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:26]([NH:29][CH2:30][C:31]1[N:17]([CH:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[C:13]2[CH:12]=[CH:11][C:10]([C:8]3[O:9][C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:24][C:6]=4[N:7]=3)=[CH:16][C:14]=2[N:15]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 674984215-Chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazoleHCID 86664950Ethyl 2-acetylaminoacetimidate hydrochloride

Product 1

HCID 674982542-Acetylaminomethyl-5-(5-chlorobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 21.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 ethanol (5 mL) was added ethyl 2-acetylaminoacetimidate hydrochloride (263 mg, 1.45 mmol), and this was heated to reflux 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 (65.2 mg, 21% yield) as white crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 2 hours
  3. filtrationthis was filtered
  4. washwashed with water
  5. customThe crystals obtained
  6. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ee6168848f5640d6b0772d317c65c0e2
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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