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Isopropylamine → 2-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid iso-propylamide

HRID 1923543
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1923543
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.[CH2:9]([C:13]1[C:17]([CH2:18][CH2:19][C:20]2[S:21][C:22]([C:26](O)=[O:27])=[C:23]([CH3:25])[N:24]=2)=[C:16]([CH3:29])[O:15][N:14]=1)[CH2:10][CH2:11][CH3:12]>O1CCOCC1.C1(C)C=CC=CC=1>[CH:1]([NH:4][C:26]([C:22]1[S:21][C:20]([CH2:19][CH2:18][C:17]2[C:13]([CH2:9][CH2:10][CH2:11][CH3:12])=[N:14][O:15][C:16]=2[CH3:29])=[N:24][C:23]=1[CH3:25])=[O:27])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 666436692-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid

Produkt 1

HCID 497820372-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid iso-propylamideAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140
Toluene
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of isopropylamine (77 mg, 1.3 mmol) in dioxane (3 mL) under argon and at room temperature was added trimethylaluminium (0.65 mL of a 2M solution in toluene, 1.3 mmol). After 1 h, a solution of 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid (100 mg, 0.32 mmol) in dioxane (4 mL) was added and the reaction mixture heated at 90° C. overnight. 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 5% methanol in dichloromethane) gave the title compound (50 mg, 44%) as a light yellow oil. MS: m/e=350.5 [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 5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-d44bd3e46c1b44eabe2876078a11c2f2
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178522B2

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