Tetrahydrofuran → (5-{5-[3-Chloro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-2-thienyl)methanol

HRID 2247712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2247712
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:5]([OH:7])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Si]([O:48][CH2:49][C:50]1[S:54][C:53]([C:55](=[N:57]O)[NH2:56])=[C:52]([CH2:59][CH3:60])[CH:51]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:57]=[C:55]([C:53]3[S:54][C:50]([CH2:49][OH:48])=[CH:51][C:52]=3[CH2:59][CH3:60])[N:56]=2)[CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1

Komponenten

7

Edukt 6

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 630873163-Chloro-4-(3-fluorophenoxy)benzoic acidHCID 725011755-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N'-hydroxythiophene-2-carboximidamide

Produkt 1

HCID 68525419(5-{5-[3-Chloro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-2-thienyl)methanol

Versuchsvorschrift

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 5 (5a) using 3-chloro-4-(3-fluorophenoxy)benzoic acid (0.14 g, 0.53 mmol) that was obtained in Example 16 (16a), 1-hydroxybenzotriazole (0.086 g, 0.56 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.11 g, 0.56 mmol), 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N′-hydroxythiophene-2-carboximidamide (0.16 g, 0.51 mmol) that was obtained in Example 10 (10d), and 1.0M solution of tetrabutylammoniumfluoride in tetrahydrofuran (1.0 mL, 1.0 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (2:8 to 5:5) as the eluent to afford the title compound (0.17 g) in a yield of 89% as a pale yellowish crystalline solid.

Aufarbeitung

  1. customthe reaction similar to

Quellen und Nachweise

ORD-Eintrag
ord-fff068e8a2244f0b9e0fb9b52d8ee061
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687491B2

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