Sulfuric acid magnesium salt (1:1) → Diethyl (2-(2-(2-(2-((3-amino-2-chloroquinolin-4-yl)amino)ethoxy)ethoxy)ethoxy)ethyl)phosphonate
Reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[O-]S([O-])(=O)=O.[Mg+2]>CCOC(C)=O>[NH2:12][C:11]1[C:2]([Cl:1])=[N:3][C:4]2[C:9]([C:10]=1[NH:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][P:27](=[O:34])([O:28][CH2:29][CH3:30])[O:31][CH2:32][CH3:33])=[CH:8][CH:7]=[CH:6][CH:5]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of diethyl (2-(2-(2-(2-((2-chloro-3-nitroquinolin-4-yl)amino)ethoxy)ethoxy)ethoxy)ethyl)phosphonate (1 equiv.) in EtOAc (0.10 M) was added 10% PUC (5% equiv. by weight) and MgSO4 (2 equiv.) in a Paar Shaker Flask. The reaction mixture was placed in a Paar Shaker at 40 psi for 7 h. At this point the reaction mixture was passed through a pad of Celite, washing with a 2:1 mixture of CHCl3:MeOH. The combined organic layers were dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by a COMBIFLASH™ system using a gradient of 0-10% MeOH/DCM to provide the title compound (97%) as a solid.
Workup
- washwashing with a 2:1 mixture of CHCl3
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- customthe volatiles were removed in vacuo
- customThe resulting residue was purified by a COMBIFLASH™ system
Sources & evidence
- ORD record
- ord-60fddaaf64fe4a2e8e71974cc8b78bef
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315530B2
Reaction notes
Loading…