2-Furancarboxylic acid, hydrazide → 5-(3-Chloro-phenyl)-3-(5-furan-2-yl-4-isobutyl-4H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]oxadiazole

HRID 273154

Reaktionsgleichung

Reaktionsgleichung von HRID 273154
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][NH2:9])=O.[N:10]([CH2:13][CH:14]([CH3:16])[CH3:15])=[C:11]=[S:12].Cl[CH2:18][C:19]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[O:21][N:20]=1>>[Cl:30][C:26]1[CH:25]=[C:24]([C:22]2[O:21][N:20]=[C:19]([CH2:18][S:12][C:11]3[N:10]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)=[N:8][N:9]=3)[N:23]=2)[CH:29]=[CH:28][CH:27]=1

Komponenten

4

Edukt 3

HCID 187312-Furancarboxylic acid, hydrazideHCID 68960Isobutyl isothiocyanateHCID 100825203-(Chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole

Produkt 1

HCID 670708805-(3-Chloro-phenyl)-3-(5-furan-2-yl-4-isobutyl-4H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]oxadiazole

Versuchsvorschrift

The title compound was synthesized according to the method described by Graybill et al. Tetrahedron lett. 2002 43, 5305-5309 from furan-2-carboxylic acid hydrazide (55.2 mg, 0.44 mmol), 1-isothiocyanato-2-methyl-propane (47 ml, 0.38 mmol) and 3-chloromethyl-5-(3-chloro-phenyl)-[1,2,4]oxadiazole (45.0 mg, 0.20 mmol) with P-BEMP (136 mg, 0.30 mmol) as base. Purification by flash chromatography (33-66% EtOAc in heptane) gave the product as an oil (12.7 mg, 15.6%). 1H NMR (CDCl3) d (ppm): 8.08 (s, 1H), 7.97 (d, 1H), 7.55 (d, 2H), 7.45 (t, 1H), 7.10 (d, 1H), 6.56 (d, 1H), 4.62 (s, 2H), 4.01 (d, 2H), 2.03 (m, 1H), 0.86 (d, 6H).

Aufarbeitung

  1. customPurification by flash chromatography (33-66% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-a322391b185147bf9e9dcf4b7de7331b
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456200B2

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