Reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH3:19])[N:7]2[CH:16]1[CH2:18][CH2:17]1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][CH2:31][CH2:32][NH2:33].C(N(CC)CC)C.[NH4+].[Cl-]>CS(C)=O.O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:33][CH2:32][CH2:31][NH:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH3:19])[N:7]2[CH:16]1[CH2:17][CH2:18]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-2-methyl-4-oxoquinoline-3-carboxylic acid (140 mg, 0.432 mmol), N-2-pyridyl-1,2-ethanediamine (88.9 mg, 0.648 mmol) and triethylamine (0.0903 mL, 0.648 mmol) in DMSO (4 mL) was stirred at 100° C. for 2 h. To the reaction mixture, water and NH4Cl was added to neutralize and the suspension was stirred for 30 min. The crude product was extracted with EtOAc, washed with brine, dried over MgSO4 and the sovent was removed in vacuo. The crude product was purified by preparative thin layer chromatography (Hexane:EtOAc 1:4) to yield 5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-2-methyl-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (79.9 mg, 42%) as a yellow amorphous solid.
Workup
- extractionThe crude product was extracted with EtOAc
- washwashed with brine
- dry with materialdried over MgSO4
- customthe sovent was removed in vacuo
- customThe crude product was purified by preparative thin layer chromatography (Hexane:EtOAc 1:4)
Sources & evidence
- ORD record
- ord-381aba9d66aa4c8bac901bfbe289bb89
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063221B2
Linked notes
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