Pyridine → n-(4-Chlorobenzyl)-8-fluoro-6-(hydrazinocarbothioyl)-4-hydroxy-3-quinolinecarboxamide
Reaction equation
[NH2:1][C:2](=[S:26])[C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([F:13])[CH:12]=1)[N:9]=[CH:8][C:7]([C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:15])=[C:6]2[OH:25].C1COCC1.C(Cl)Cl.O(C)S(C(F)(F)F)(=O)=O.[N:44]1C=CC=CC=1>>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][NH:16][C:14]([C:7]2[CH:8]=[N:9][C:10]3[C:5]([C:6]=2[OH:25])=[CH:4][C:3]([C:2]([NH:1][NH2:44])=[S:26])=[CH:12][C:11]=3[F:13])=[O:15])=[CH:19][CH:20]=1Participants
6
Procedure
To a suspension of the title compound of Example 52 (0.60 g) in 20 mL 1:1 THF:CH2Cl2 at room temperature is added methyl triflate (0.2 mL). The reaction is stirred for 45 minutes after which time everything goes into solution. Pyridine (0.38 mL) is added and then H2S is bubbled in for 1 hour. Nitrogen is then purged through the reaction for 30 minutes. Hydrazine monohydrate (0.28 mL) is added dropwise to the reaction mixture. The reaction is stirred for 1 hour after which time the solution turned from an orange to a pale yellow color and a precipitate is observed. The solid in the reaction is filtered and dried to give the desired product (0.26 g).
Workup
- customH2S is bubbled in for 1 hour
- customNitrogen is then purged through the reaction for 30 minutes
- additionHydrazine monohydrate (0.28 mL) is added dropwise to the reaction mixture
- stirringThe reaction is stirred for 1 hour after which time the solution
- filtrationThe solid in the reaction is filtered
- customdried
Sources & evidence
- ORD record
- ord-7f6fb0c5a4e742329465666b8f73ee2b
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093732
Reaction notes
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