7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839362, compound
Reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]([CH:10]3[CH2:15][NH:14][CH2:13][CH2:12][NH:11]3)=[C:8]([CH3:9])[C:4]=2[CH:3]=1.Cl[C:19]1[CH:28]=[C:27]2[C:22]([C:23](=[O:34])[C:24]([C:31]([OH:33])=[O:32])=[CH:25][N:26]2[CH2:29][CH3:30])=[CH:21][C:20]=1[F:35]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[S:6][C:7]([CH:10]3[NH:11][CH2:12][CH2:13][N:14]([C:19]4[CH:28]=[C:27]5[C:22]([C:23](=[O:34])[C:24]([C:31]([OH:33])=[O:32])=[CH:25][N:26]5[CH2:29][CH3:30])=[CH:21][C:20]=4[F:35])[CH2:15]3)=[C:8]([CH3:9])[C:4]=2[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 3.0 g portion of 2-(5-chloro-3-methylbenzo[b]thien-2-yl)piperazine was added to 5 ml of pyridine. A 1.01 g portion of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was added and the mixture was heated in a pressure bottle, under argon at 130°-135° C. for 18 hours, then cooled and placed in an ice bath. The resulting crystals were collected, washed with cold pyridine, dichloromethane and ether and recrystallized from dimethylformamide, giving 401 mg of the desired product, mp 300°-305° C.