2-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole → 2-Methyl-5-(6-aminobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74218
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17]3[O:18][C:19]4[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:16][C:4]=2[N:3]=1.[H][H]>[Pd].CO>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17]3[O:18][C:19]4[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:16][C:4]=2[N:3]=1

Komponenten

5

Edukt 2

HCID 674986292-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 674987622-Methyl-5-(6-aminobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

2-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 47-2) (135 mg, 0.357 mmol) was added to methanol (20 mL) containing palladium/carbon (Pd: 10%, 0.06 g), hydrogen was substituted in by successively reducing the pressure and purging with hydrogen gas 3 times, and this was stirred at room temperature for 2.5 hours. After substituting in nitrogen, the insoluble material was filtered off through a Celite layer (20 mm thickness), and this same layer was washed with methanol (20 mL, 3 times). The filtrate was combined with the wash solutions and the solvent was distilled out at reduced pressure, the residue obtained was purified by silica gel column chromatography to yield the title compound (50 mg, 40.2% yield) as brown crystals.

Aufarbeitung

  1. custompurging with hydrogen gas 3 times
  2. filtrationthe insoluble material was filtered off through a Celite layer (20 mm thickness)
  3. washthis same layer was washed with methanol (20 mL, 3 times)
  4. distillationthe solvent was distilled out at reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-833e975568284f908dc7e5138b34377f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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