4-Aminotetrahydropyran → 4-Methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (tetrahydro-pyran-4-yl)-amide

HRID 1923492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1923492
[NH2:1][CH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C[Al](C)C.[CH3:12][C:13]1[N:14]=[C:15]([CH2:21][CH2:22][C:23]2[C:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:25][O:26][C:27]=2[CH3:28])[S:16][C:17]=1[C:18](O)=[O:19]>O1CCOCC1.C1(C)C=CC=CC=1>[O:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:18]([C:17]2[S:16][C:15]([CH2:21][CH2:22][C:23]3[C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:25][O:26][C:27]=3[CH3:28])=[N:14][C:13]=2[CH3:12])=[O:19])[CH2:3][CH2:4]1

Komponenten

6

Edukt 3

HCID 4192234-AminotetrahydropyranHCID 16682925TrimethylaluminumHCID 66643564HCID 66643564, Verbindung

Produkt 1

HCID 497829294-Methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (tetrahydro-pyran-4-yl)-amideAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred suspension of 4-aminotetrahydropyran (123 mg, 1.2 mmol) in dioxane (5 mL) under argon at room temperature was added trimethylaluminium (0.6 mL of a 2M solution in toluene, 1.2 mmol). After 1 h, a solution of 4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (100 mg, 0.3 mmol) in dioxane (5 mL) was added and the reaction mixture warmed to 90° C. After 3 h, the reaction mixture was 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 10% methanol in dichloromethane) gave the title compound (40 mg, 32%) as a colourless oil. MS: m/e=412.4 [M+H]+.

Aufarbeitung

  1. waitAfter 3 h
  2. temperaturethe reaction mixture was cooled
  3. customquenched with ice water
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with Seignette's salt solution
  6. customthen dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by chromatography (silica, 0 to 10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-a684b76f99924f9cab01d0d776e606ca
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178522B2

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