HCID 54470582, compound → (RS)-1-cyclopropyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine-3-carboxylic acid

HRID 344906Notes

Reaction equation

HRID 344906 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15]([N:19]5[CH2:24][CH2:23][NH:22][CH:21]([C:25]6[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=6)[CH2:20]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:33])[C:6]([C:34]([O:36]CC)=[O:35])=[CH:5]2)[CH2:3][CH2:2]1>[OH-].[K+].C(O)C>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15]([N:19]5[CH2:24][CH2:23][NH:22][CH:21]([C:25]6[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=6)[CH2:20]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:33])[C:6]([C:34]([OH:36])=[O:35])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 54470582HCID 54470582, compound

Product 1

HCID 53972680(RS)-1-cyclopropyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine-3-carboxylic acidYield 105.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

(RS)-1-Cyclopropyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 29, but starting with (RS)-1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.5 g) in N aqueous potassium hydroxide (18.4 cc) and ethanol (18.4 cc). After 1 recrystallization in dimethylformamide (50 cc), (RS)-1-cyclopropyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine-3-carboxylic acid (1.5 g) is obtained in the form of a yellow solid, decomposing at 287° C.

Workup

  1. custom(RS)-1-Cyclopropyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 29
  2. customAfter 1 recrystallization in dimethylformamide (50 cc)

Sources & evidence

ORD record
ord-f02b6b31cd3943e89f351c9b03061b39
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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