Phenylacetaldehyde → 5-(Benzoxazol-2-yl)-2-benzyl-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74234

Reaktionsgleichung

Reaktionsgleichung von HRID 74234
[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:24]1([CH2:30][CH:31]=O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[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:31]([CH2:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:15][C:14]=2[CH:16]=1

Komponenten

6

Edukt 4

HCID 998PhenylacetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Produkt 1

HCID 674980805-(Benzoxazol-2-yl)-2-benzyl-1-(tetrahydropyran-4-yl)benzimidazoleAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

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 dimethylformamide (3 mL) was added phenylacetaldehyde (101 mg, 0.840 mmol) and oxone (258 mg, 0.420 mmol), and this was stirred at room temperature for 3 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 (110 mg, 42% yield) as light brown amorphous mass.

Aufarbeitung

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0bbbe93463ce44a8911d4cac7a6abf1f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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