HCID 19423693, compound → HCID 19423638, compound

HRID 743656Notes

Reaction equation

HRID 743656 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.[CH3:33][C:34]1([NH:38][CH3:39])[CH2:37][NH:36][CH2:35]1>>[CH2:18]([N:8]1[C:7]2[N:6]=[C:5]3[CH:20]=[C:21]([N:36]4[CH2:37][C:34]([CH3:33])([NH:38][CH3:39])[CH2:35]4)[C:2]([F:1])=[CH:3][C:4]3=[CH:13][C:12]=2[C:11](=[O:14])[C:10]([C:15]([OH:17])=[O:16])=[CH:9]1)[CH3:19]

Participants

3

Reactant 2

HCID 19423693HCID 19423693, compoundHCID 194237363-Methyl-3-(methylamino)azetidine dimethanesulphonate

Product 1

HCID 19423638HCID 19423638, compoundYield 61.4%

Procedure

1-Ethyl-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 1.52 g of 7,8-difluoro-1-ethyl-4-oxo-1,4-dihydrobenzo[b]-[1,8]naphthyridine-3-carboxylic acid and 2.34 g of 3-methyl-3-(methylamino)azetidine dimethanesulphonate. 1.18 g of 1-ethyl-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 338° C.

Workup

  1. custom1-Ethyl-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-1a15f31c8b064f95a5285e868d038618
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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