Sodium Bicarbonate → 5-(Benzoxazol-2-yl)-2-(3-methoxyphenyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74237Notes

Reaction equation

HRID 74237 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.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=1)[C:30](=N)OCC.C(=O)([O-])O.[Na+]>CO>[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:30]([C:29]3[CH:35]=[CH:36][CH:37]=[C:27]([O:26][CH3:25])[CH:28]=3)=[N:15][C:14]=2[CH:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12282163Benzenecarboximidic acid, 3-methoxy-, ethyl ester, hydrochlorideHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 674985095-(Benzoxazol-2-yl)-2-(3-methoxyphenyl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (200 mg, 0.646 mmol) in methanol (5 mL) was added ethyl 3-methoxybenzimidate hydrochloride (153 mg, 0.711 mmol), and this was stirred at room temperature for 8 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with chloroform. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The crystals obtained were purified by silica gel column chromatography to yield the title compound (216 mg, 79% yield) as light brown crystals.

Workup

  1. extractionthis was extracted with chloroform
  2. customAfter the organic layer obtained
  3. dry with materialwas dried over anhydrous sodium sulfate, it
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customThe crystals obtained
  7. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-37e85f1a7b404d0b9dc3309c32dcd52b
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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