Hydrochloric Acid → HCID 178457104, Verbindung

HRID 1405314

Reaktionsgleichung

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]#[N:26])[CH:16]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[N:27]([Na])=[N+:28]=[N-:29].Cl>CS(C)=O.O.Br[Zn]Br>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12]([N:11]=3)=[CH:13][CH:14]=[C:15]([C:25]3[NH:29][N:28]=[N:27][N:26]=3)[CH:16]=4)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

To a solution of 2-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrile (150 mg, 0.44 mmol) in DMSO (15 ml) was added dibromozinc (50 mg, 0.22 mmol), azidosodium (86 mg, 1.32 mmol), and water (2 ml), and the resulting mixture was stirred overnight at 130° C. in an oil bath. The solution was diluted with water (200 ml) and adjusted to pH 4 with HCl (2N), extracted with ethyl acetate (5×50 ml), dried over anhydrous magnesium, and concentrated in vacuo to give a residue, which was purified by a silica gel column (10% methanol in dichloromethane) to afford 3-(1H-indazol-5-yl)-N-methyl-N-(propan-2-yl)-7-(1H-tetrazol-5-yl)quinoxalin-2-amine as a yellow solid (38.5 mg, 23%).

Aufarbeitung

extractionextracted with ethyl acetate (5×50 ml)
dry with materialdried over anhydrous magnesium
concentrationconcentrated in vacuo
customto give a residue, which
customwas purified by a silica gel column (10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag: ord-861a1c89cc074420a88955b33776b988
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08916561B2

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