Propanoic acid, 3-ethoxy-3-imino-, ethyl ester → 5-(Benzoxazol-2-yl)-2-(ethoxycarbonylmethyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74266Notes

Reaction equation

HRID 74266 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].C(O[C:27](=N)[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])C.C(=O)([O-])O.[Na+]>C(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]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N:15][C:14]=2[CH:16]=1

Participants

5

Reactant 3

HCID 75346Propanoic acid, 3-ethoxy-3-imino-, ethyl esterHCID 516892Sodium BicarbonateHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 867627065-(Benzoxazol-2-yl)-2-(ethoxycarbonylmethyl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 ethanol (5 mL) was added ethyl 3-ethoxy-3-iminopropionate (190 mg, 0.969 mmol), and this was heated to reflux for 2 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with ethyl acetate. 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 (249 mg, 95% yield) as gray crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 2 hours
  3. extractionthis was extracted with ethyl acetate
  4. customAfter the organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate, it
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customThe crystals obtained
  9. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dfd5be66472846298a55e4327a71616f
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

Loading…