Triethylamine → 3-Ethoxycarbonyl-1-(2-fluoroethyl)-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine
Reaction equation
Cl[C:2]1[C:11]([C:12]([C:14](=[CH:20][N:21]([CH3:23])C)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([F:26])[C:6]([F:25])=[C:7]([F:24])[CH:8]=2)[N:3]=1.Cl.[F:28][CH2:29]CN.C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1>C(O)C>[CH2:18]([O:17][C:15]([C:14]1[C:12](=[O:13])[C:11]2[CH:10]=[C:9]3[CH:8]=[C:7]([F:24])[C:6]([F:25])=[C:5]([F:26])[C:4]3=[N:3][C:2]=2[N:21]([CH2:23][CH2:29][F:28])[CH:20]=1)=[O:16])[CH3:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Ethoxycarbonyl-1-(2-fluoroethyl)-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under conditions similar to Example 3, but starting with ethyl 2-(2-chloro-6,7,8-trifluoro-3-quinolinecarbonyl)(dimethylamino)acrylate (3.9 g), 2-fluoroethylamine hydrochloride (3 g) and triethylamine (4.2 cc) in ethanol (100 cc). After the addition of DBU (1.8 cc), the solution is heated for 2 hours to 80° C. After the same treatment of the reaction mixture as in Example 24, 3-ethoxycarbonyl-7,8,9-trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (2.8 g) is obtained in the form of a yellow solid, m.p. 302°-304° C.
Workup
- custom3-Ethoxycarbonyl-1-(2-fluoroethyl)-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under conditions similar to Example 3
- temperaturethe solution is heated for 2 hours to 80° C
Sources & evidence
- ORD record
- ord-2935ac97332e4db6a57d92aaae066443
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05053509
Reaction notes
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