1-Cyclopropyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid → 1-Cyclopropyl-7-fluoro-8-(3-methyl-3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 743655Notes

Reaction equation

HRID 743655 reaction equation
[F:1][C:2]1[C:22](F)=[CH:21][C:5]2=[N:6][C:7]3[N:8]([CH:18]4[CH2:20][CH2:19]4)[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.[CH3:34][C:35]1([NH:39][CH3:40])[CH2:38][NH:37][CH2:36]1>>[CH:18]1([N:8]2[C:7]3[N:6]=[C:5]4[CH:21]=[C:22]([N:37]5[CH2:38][C:35]([CH3:34])([NH:39][CH3:40])[CH2:36]5)[C:2]([F:1])=[CH:3][C:4]4=[CH:13][C:12]=3[C:11](=[O:14])[C:10]([C:15]([OH:17])=[O:16])=[CH:9]2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 148533411-Cyclopropyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidHCID 194237363-Methyl-3-(methylamino)azetidine dimethanesulphonate

Product 1

HCID 194237081-Cyclopropyl-7-fluoro-8-(3-methyl-3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidYield 79.3%

Procedure

1-Cyclopropyl-7-fluoro-8-(3-methyl-3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 15, but starting with 1.58 g of 7,8-difluoro-1-cyclopropyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 2.34 g of 3-methyl-3-(methylamino)azetidine dimethanesulphonate. 1.57 g of 1-cyclopropyl-7-fluoro-8-(3-methyl-3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid, which decomposes at 330° C.

Workup

  1. custom1-Cyclopropyl-7-fluoro-8-(3-methyl-3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 15

Sources & evidence

ORD record
ord-181f0a4c1131429d9f49795bfec0f540
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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