Amantadine → 2-(2-(1-Adamantylamino)anilin-5-yl)benzoxazole

HRID 74205

Reaktionsgleichung

Reaktionsgleichung von HRID 74205
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.C(=O)([O-])O.[Na+].[C:25]12([NH2:35])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.[H][H]>C(O)C.[C].[Pd].O1CCCC1.O>[C:25]12([NH:35][C:2]3[CH:7]=[CH:6][C:5]([C:8]4[O:9][C:10]5[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=5[N:12]=4)=[CH:4][C:3]=3[NH2:17])[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2

Komponenten

9

Edukt 4

HCID 2130AmantadineHCID 516892Sodium BicarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 674988422-(2-(1-Adamantylamino)anilin-5-yl)benzoxazoleAusbeute 16,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added sodium hydrogen carbonate (195 mg, 2.32 mmol) and 1-adamantylamine (185 mg, 1.22 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered off, washed with water and then dried. The crystals obtained were added to a tetrahydrofuran (5 mL) solution containing 10% palladium-carbon (100 mg), a hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 6 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (67.0 mg, 16% yield) as brown crystals.

Aufarbeitung

  1. temperaturethis was heated
  2. temperatureto reflux
  3. filtrationthe precipitated crystals were filtered off
  4. washwashed with water
  5. customdried
  6. customThe crystals obtained
  7. stirringthis was stirred at room temperature for 6 hours
  8. filtrationthis was filtered through Celite
  9. concentrationthe filtrate was concentrated
  10. customThe residue obtained
  11. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-017b0ca703ea443186c20c805724ba80
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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