Amantadine → Adamantan-1-yl-[2-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-amine

HRID 8671

Reaktionsgleichung

Reaktionsgleichung von HRID 8671
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[O:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[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>C(#N)C>[C:25]12([NH:35][CH2:2][CH2:3][O:4][C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([C:11]4[C:15]5[S:16][CH:17]=[CH:18][C:14]=5[O:13][N:12]=4)[CH:6]=3)[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2

Komponenten

5

Edukt 3

HCID 2130AmantadineHCID 11430Potassium CarbonateHCID 219835823-[3-(2-Bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole

Produkt 1

HCID 21983590Adamantan-1-yl-[2-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The title compound is prepared from 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole, potassium carbonate, 1-adamantanamine and acetonitrile essentially as described above in example 18 except that the reaction is run overnight and the compound is purified by column chromatography using a graded solvent mixture of 5% ethyl acetate in DCM to 10% methanol in ethyl acetate. Purity by LC/MS (APCI)=97%, [M+H]+=395.

Aufarbeitung

  1. customthe compound is purified by column chromatography
  2. additiona graded solvent mixture of 5% ethyl acetate in DCM to 10% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fb43606501f3400b8d4cf5f8ac7ab8df
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091199B1

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