3-(Chloromethyl)-5-(thiophen-2-yl)-1,2,4-oxadiazole → HCID 69142773, Verbindung

HRID 1794123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1794123
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][OH:5].Cl[CH2:13][C:14]1[N:18]=[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[O:16][N:15]=1.[CH3:24][C@@H:25]1[CH2:30][NH:29][CH2:28][CH2:27][N:26]1[C:31](OCC1C=C(OCC=C)C=CC=1F)=[O:32]>>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:13][C:14]2[N:18]=[C:17]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[O:16][N:15]=2)[CH:7]=[C:6]([F:11])[C:3]=1[CH2:4][O:5][C:31]([N:26]1[CH2:27][CH2:28][NH:29][CH2:30][C@H:25]1[CH3:24])=[O:32]

Komponenten

4

Edukt 3

HCID 27983433-(Chloromethyl)-5-(thiophen-2-yl)-1,2,4-oxadiazoleHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenolHCID 69142358HCID 69142358, Verbindung

Produkt 1

HCID 69142773HCID 69142773, Verbindung

Versuchsvorschrift

(R)-2-Methyl-piperazine-1-carboxylic acid 2,6-difluoro-4-(5-thiophen-2-yl-[1,2,4]oxadiazol-3-ylmethoxy)-benzyl ester was prepared from 2,6-difluoro-4-hydroxybenzyl alcohol, 3-chloromethyl-5-thiophen-2-yl-[1,2,4]oxadiazole and (R) 2-methylpiperazine resin according to the methods described for Example 126 to give the product as a yellow oil: δH(400 MHz; d6-DMSO) 1.10 (3H, d, J 7.0 Hz), 2.40 (1H, td, J 12.0, 3.5 Hz), 2.62 (2H, br d, J, 2.5 Hz), 2.75–2.82 (1H, br d, J 12 Hz), 2.88 (1H, td, J 12.5, 3.5 Hz), 3.55 (1H, br d, J 12 Hz), 3.96 (1H, br s), 5.02 (1H, d, J 12.5 Hz), 5.07 (1H, d, J 12.5 Hz), 5.42 (2H, s), 6.93–7.01 (2H, m), 7.36(1H, dd, J 5.0 and 4 Hz), 8.06 (1H, dd, J4, 1.0 Hz) and 8.12 (1H, dd, J 5.0, 1 Hz); HPLC (XTERRA, 50–80%, 235 nm) 99.8% (4.22 min).

Quellen und Nachweise

ORD-Eintrag
ord-7eb547e192a9435393b1b860e240d884
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022707B2

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