HCID 19423693, compound → HCID 19423704, compound
Reaction equation
[F:1][C:2]1[C:21](F)=[CH:20][C:5]2=[N:6][C:7]3[N:8]([CH2:18][CH3:19])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.CS(O)(=O)=O.CS(O)(=O)=O.[NH2:33][C:34]1([CH3:38])[CH2:37][NH:36][CH2:35]1>>[NH2:33][C:34]1([CH3:38])[CH2:37][N:36]([C:21]2[C:2]([F:1])=[CH:3][C:4]3[C:5]([CH:20]=2)=[N:6][C:7]2[N:8]([CH2:18][CH3:19])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=2[CH:13]=3)[CH2:35]1Participants
Procedure
8-(3-Amino-3-methyl-1-azetidinyl)-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions described in Example 15, but starting with 1.52 g of 7,8-difluoro-1-ethyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid and 2.22 g of 3-amino-3-methylazetidine dimethanesulphonate, for 72 hours at approximately 20° C. and then 1 and a half hours at a temperature in the region of 90° C. The insoluble matter in the reaction mixture is drained at approximately 20° C., washed with twice 20 cm3 of water, recrystallized in 70 cm3 of dimethylformamide and washed with 40 cm3 of ethanol at approximately 75° C. 1.45 g of 8-(3-Amino-3-methyl-1-azetidinyl)-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid, which decomposes at 334° C.
Workup
- custom8-(3-Amino-3-methyl-1-azetidinyl)-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions
- custom1 and a half hours
- customin the region of 90° C
- customis drained at approximately 20° C.
- washwashed with twice 20 cm3 of water
- customrecrystallized in 70 cm3 of dimethylformamide
- washwashed with 40 cm3 of ethanol at approximately 75° C
Sources & evidence
- ORD record
- ord-bf42633ed16f4c6daaccde4ea8e0fb81
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05556861
Reaction notes
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