Dichloromethane → 4-Oxo-N-[3-[2-(1-piperidyl)ethylsulfonylamino]-5-(trifluoromethyl)phenyl]-1H-quinoline-3-carboxamide
Reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([NH:14][C:15]1[CH:20]=[C:19]([NH:21][S:22]([CH:25]=[CH2:26])(=[O:24])=[O:23])[CH:18]=[C:17]([C:27]([F:30])([F:29])[F:28])[CH:16]=1)=[O:13].[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C(Cl)Cl>C(O)(C)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([NH:14][C:15]1[CH:16]=[C:17]([C:27]([F:29])([F:30])[F:28])[CH:18]=[C:19]([NH:21][S:22]([CH2:25][CH2:26][N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)(=[O:24])=[O:23])[CH:20]=1)=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A mixture of 4-oxo-N-[3-(trifluoromethyl)-5-(vinylsulfonamido)phenyl]-1,4-dihydroquinoline-3-carboxamide (50 mg, 0.11 mmol), piperidine (18 μL, 1.6 eq) and LiClO4 (20 mg, 1.7 eq) was suspended in a 1:1 solution of CH2Cl2:isopropanol (1.5 mL). The mixture was refluxed at 75° C. for 18 h. After this time, LCMS analysis showed >95% conversion to the desired product. The crude mixture was purified by reverse-phase HPLC to provide 4-oxo-N-[3-[2-(1-piperidyl)ethylsulfonylamino]-5-(trifluoromethyl)phenyl]-1H-quinoline-3-carboxamide (318) as a yellowish solid (15 mg, 25%). 1H-NMR (d6-Acetone, 300 MHz) δ 8.92 (br s, 1H), 8.4 (d, J=8.1 Hz, 1H), 8.05 (br s, 1H), 7.94 (br s, 1H), 7.78 (br s, 2H), 7.53-751 (m, 1H), 7.36 (br s, 1H), 3.97 (t, J=7.2 Hz, 2H), 3.66 (t, J=8 Hz, 2H), 3.31-3.24 (m, 6H), 1.36-1.31 (m, 4H); ESI-MS 489.1 m/z (MH+).
Sources & evidence
- ORD record
- ord-04a6e519cc504b42a4bc2925476cc0d4
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802700B2
Reaction notes
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