Tert-Butylamine → HCID 89781992, Verbindung

HRID 1056107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056107
F[C:2]1[C:3]([CH3:15])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:7][CH:6]=2.[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17]>CS(C)=O>[C:16]([NH:20][C:2]1[C:3]([CH3:15])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:7][CH:6]=2)([CH3:19])([CH3:18])[CH3:17]

Komponenten

4

Edukt 2

HCID 6385Tert-ButylamineHCID 897818641-(3-Fluoro-2-methylquinoxalin-5-yl)ethanone

Produkt 1

HCID 89781992HCID 89781992, VerbindungAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a stirred solution of 1-(3-fluoro-2-methylquinoxalin-5-yl)ethanone (126g) (13 g, 63.7 mmol) in DMSO (100 mL) was added t-BuNH2 (33.7 mL, 318 mmol). The reaction mixture was heated in an oil bath at 65° C. for 4 h. It was cooled to RT, treated with 100 mL of ice cold water. The precipitated light orange solid was collected, washed with water (2×15 mL), dried in a vacuum oven at 35° C. for 18 h to give 1-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)ethanone (606a) (14.96 g, 91% yield) which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 7.90 (dd, J=8.12, 1.66 Hz, 1H), 7.76 (dd, J=7.34, 1.66 Hz, 1H), 7.35 (t, J=7.73 Hz, 1H), 4.81 (br., 1H), 2.88 (s, 3H), 2.53 (s, 3H), 1.57 (s, 9H). m/z (ESI, +ve) 258.2 (M+H)+.

Aufarbeitung

  1. temperatureIt was cooled to RT
  2. customThe precipitated light orange solid was collected
  3. washwashed with water (2×15 mL)
  4. customdried in a vacuum oven at 35° C. for 18 h

Quellen und Nachweise

ORD-Eintrag
ord-330d25992c3448618bdeed759fc73ae5
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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