Brimonidine → N-(4,5-dihydro-1H-imidazol-2-yl)-5-methylquinoxalin-6-amine

HRID 430458

Reaktionsgleichung

Br[C:2]1[C:11]([NH:12][C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2.[CH3:18][Sn](C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[CH3:18][C:2]1[C:11]([NH:12][C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2

Komponenten

Reaktionsbedingungen

Temperatur: 145 °C

Versuchsvorschrift

A sealable reaction tube was charged with 5-bromo-6-(2-imidazolin-2-ylamino) quinoxaline (104 mg., 0.36 mmol) (prepared as noted above), tetramethyl tin (214 mg., 1.2 mmol) and (Ph3P)2PdCl2 (10 mg) and dry dimethylformamide (2 ml) in a reaction tube. The reaction mixture was purged with dry nitrogen gas. The tube was sealed and heated to 145° C. for 6 hours. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The dark brown residue was chromatographed (SiO2; 5/1 CHCl3/CH3OH saturated with NH3 (g)) to yield 46.5 mg (53%) of the title compound as a light yellow solid. An analytical sample was prepared by recrystallization from CHCl3/CH3OH and had a melting point of 183-186° C. The title compound was characterized by 1H and 13CNMR and mass spectral analysis.

Aufarbeitung

customThe reaction mixture was purged with dry nitrogen gas
customThe tube was sealed
temperatureThe reaction mixture was cooled to room temperature
customthe solvent removed in vacuo
customThe dark brown residue was chromatographed (SiO2; 5/1 CHCl3/CH3OH saturated with NH3 (g))

Quellen und Nachweise

ORD-Eintrag: ord-5f2d7b429c9d42b5925b4ddc21175946
Quelldatensatz: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06323204B1

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