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

HRID 74266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74266
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 867627065-(Benzoxazol-2-yl)-2-(ethoxycarbonylmethyl)-1-(tetrahydropyran-4-yl)benzimidazoleAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dfd5be66472846298a55e4327a71616f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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