(R)-1-Pyridin-2-yl-ethylamine → 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-3-nitro-N-((R)-1-(pyridin-2-yl)ethyl)quinolin-4-amine
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C@H:30]([NH2:32])[CH3:31]>O1CCOCC1>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:32][C@@H:30]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=4)[CH3:31])=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(4-chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole (for a preparation, see Intermediate 8) (1 g, 3.00 mmol) in 1,4-dioxane (6.5 mL) was added (R)-1-(pyridin-2-yl)ethanamine (0.549 g, 4.49 mmol) and the mixture stirred at room temperature for 5 h. A further portion of (R)-1-(pyridin-2-yl)ethanamine (0.255 g, 2.25 mmol) was added and the mixture stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue purified by chromatography (50 g column, cyclohexane/EtOAc gradient) to give 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-3-nitro-N—((R)-1-(pyridin-2-yl)ethyl)quinolin-4-amine (1.15 g, 2.74 mmol, 92% yield) as an orange solid. LCMS: (Formate, 2 min), Rt 0.98 mins, MH+ 420.
Workup
- stirringthe mixture stirred at room temperature overnight
- customThe solvent was removed under reduced pressure
- customthe residue purified by chromatography (50 g column, cyclohexane/EtOAc gradient)
Sources & evidence
- ORD record
- ord-a967eeec45fa4cb4b70335c0cbb7175d
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846709B2
Reaction notes
Loading…