Acetaldehyde → 2-Methyl-5-(4-methylbenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74215
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]3[O:16][C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:11][C:9]=2[NH2:10])[CH2:3][CH2:2]1.[CH:24](=O)[CH3:25].OOS([O-])=O.[K+].[C:33](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:24][C:25]1[N:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[C:8]2[CH:14]=[CH:13][C:12]([C:15]3[O:16][C:17]4[CH:23]=[CH:22][CH:21]=[C:20]([CH3:33])[C:18]=4[N:19]=3)=[CH:11][C:9]=2[N:10]=1

Komponenten

7

Edukt 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

Produkt 1

HCID 674988722-Methyl-5-(4-methylbenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleAusbeute 20,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 46-2) (0.56 g, 1.7 mmol) in dimethylformamide (5 mL) containing water (0.18 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 90 mg, 1.8 mmol) and oxone (0.69 mg, 1.1 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 (123 mg, 20.4% yield) as light brown crystals.

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-764065c8d4984caeb5f455023038785f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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