Phenylethanolamine → 1-Phenyl-2-[3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propylamino]-ethanol

HRID 8651

Reaktionsgleichung

Reaktionsgleichung von HRID 8651
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[O:14][N:13]=2)[CH:9]=[CH:10][CH:11]=1.ClCCCOC1C=C(C2C3SC=CC=3ON=2)C=CC=1.[NH2:39][CH2:40][CH:41]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[OH:42].C(=O)([O-])[O-].[K+].[K+]>>[C:43]1([CH:41]([OH:42])[CH2:40][NH:39][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]3[C:16]4[S:17][CH:18]=[CH:19][C:15]=4[O:14][N:13]=3)[CH:7]=2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Komponenten

5

Edukt 4

HCID 1000PhenylethanolamineHCID 11430Potassium CarbonateHCID 219835563-[3-(3-Chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazoleHCID 219835593-[3-(3-Bromo-propoxy)phenyl]-thieno[2,3-d]isoxazole

Produkt 1

HCID 99525311-Phenyl-2-[3-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-propylamino]-ethanolAusbeute 100 %

Versuchsvorschrift

The title compound is prepared from a mixture of 3-[3-(3-bromo-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 3-[3-(3-chloro-propoxy)-phenyl]-thieno[2,3-d]isoxazole, 2-amino-1-phenylethanol and potassium carbonate essentially as described above in example 4 except that the column is eluted with a mixture of dichloromethane:methanol (95:5). Combine the appropriate fractions and concentrate to give the title compound (0.62 g, 100% Yield) as a solid. Purity by LC/MS (APCI)=100% area, [M+H]+=395 m/e.

Aufarbeitung

  1. washis eluted with a mixture of dichloromethane:methanol (95:5)
  2. concentrationCombine the appropriate fractions and concentrate

Quellen und Nachweise

ORD-Eintrag
ord-fb7c9101f37f44f4aa6d125230905285
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091199B1

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