Tetrahydrofuran → 6-(2-(Imino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine
Reaktionsgleichung
[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]#[N:21])[CH:8]=2)[N:3]=1.[C:27]1([Mg]Cl)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1COCC1>>[NH:21]=[C:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:19]1[CH:22]=[CH:23][CH:24]=[C:25]([CH3:26])[C:18]=1[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH2:1])[C:11]([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)=[CH:10]2Komponenten
4
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a sealed vessel containing 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile (0.10 g, 0.290 mmol, prepared as in Example 14, Step 1) was added phenylmagnesium chloride, 2.0M solution in THF (0.58 mL, 1.161 mmol). The mixture was sonicated until all solids were in solution and then warmed vessel to 60° C. for 15 h. The reaction mixture was cooled to RT and divided into two portions. The imine solution was concentrated in vacuo. The residue was taken up in 2.5 mL MeOH and purified by HPLC (10-100% MeCN/H2O with 0.1% TFA modifier) to afford 6-(2-(imino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine.