4-Aminotetrahydropyran → 2-[(e)-2-(5-Methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid(tetra-hydro-pyran-4-yl)-amide

HRID 1923561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1923561
[NH2:1][CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C[Al](C)C.C([O:14][C:15]([C:17]1[S:21][C:20](/[CH:22]=[CH:23]/[C:24]2[C:25]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:26][O:27][C:28]=2[CH3:29])=[N:19][CH:18]=1)=O)C>O1CCOCC1.C1(C)C=CC=CC=1>[O:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:15]([C:17]2[S:21][C:20](/[CH:22]=[CH:23]/[C:24]3[C:25]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[N:26][O:27][C:28]=3[CH3:29])=[N:19][CH:18]=2)=[O:14])[CH2:3][CH2:4]1

Komponenten

6

Edukt 3

HCID 4192234-AminotetrahydropyranHCID 16682925TrimethylaluminumHCID 66643683HCID 66643683, Verbindung

Produkt 1

HCID 497818072-[(e)-2-(5-Methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid(tetra-hydro-pyran-4-yl)-amideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 4-aminotetrahydropyran (123 mg, 1.22 mmol) in dioxane (3 mL) under argon and at room temperature was added trimethylaluminium (0.6 mL of a 2M solution in toluene, 1.2 mmol). After 1 h, a solution of 2-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid ethyl ester (50 mg, 0.15 mmol) in dioxane (3 mL) was added and the reaction mixture heated at 90° C. for 3 h. The reaction mixture was then cooled, quenched with ice water and extracted with dichloromethane. The combined extracts were washed with Seignette's salt solution then dried, filtered, and concentrated. Purification by chromatography (silica, 0 to 2.5% methanol in dichloromethane) gave the title compound (34 mg, 59%) as a white solid. MS: m/e=396.3 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled
  2. customquenched with ice water
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with Seignette's salt solution
  5. customthen dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica, 0 to 2.5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-e81960e92c454ae1a7622ce43806fe75
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178522B2

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