3-(Chloromethyl)-5-(thiophen-2-yl)-1,2,4-oxadiazole → HCID 69141856, Verbindung

HRID 1794124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1794124
[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.Cl[C:25]([N:27]1[C@H:32]([CH3:33])[CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][C@@H:28]1[CH3:41])=[O:26]>>[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:25]([N:27]1[C@H:32]([CH3:33])[CH2:31][NH:30][CH2:29][C@@H:28]1[CH3:41])=[O:26]

Komponenten

4

Edukt 3

HCID 27983433-(Chloromethyl)-5-(thiophen-2-yl)-1,2,4-oxadiazoleHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Produkt 1

HCID 69141856HCID 69141856, Verbindung

Versuchsvorschrift

cis-2,6-Dimethyl-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 cis-1-chlorocarbonyl-2,6-dimethyl-4-tert-butoxycarbonylpiperazine according to the methods described for Example 54 and 121 to give the product as a yellow oil: δH(400 MHz; d6-DMSO) 1.14 (6H, d, J 6.5 Hz), 2.60 (2H, dd, J 12, 5 Hz), 2.66 (2H, d, J 12 Hz), 3.77–3.87 (2H, m), 5.05 (2H, s), 5.42 (2H, s), 6.93–7.01 (2H, m), 7.36 (1H, dd, J 5.0, 4 Hz), 8.06 (1H, dd, J 4, 1.0 Hz) and 8.12 (1H, dd, J 5.0, 1.0 Hz); HPLC (XTERRA, 50–80%, 235 nm) 99.4% (5.04 min).

Quellen und Nachweise

ORD-Eintrag
ord-f5cf49f59ea346f5be9058d5ca224ca0
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022707B2

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