7,8-Difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid → HCID 19423732, compound

HRID 743666Notes

Reaction equation

HRID 743666 reaction equation
[F:1][C:2]1[C:20](F)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[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.[NH2:32][C:33]1([CH2:37][CH3:38])[CH2:36][NH:35][CH2:34]1>>[NH2:32][C:33]1([CH2:37][CH3:38])[CH2:36][N:35]([C:20]2[C:2]([F:1])=[CH:3][C:4]3[C:5]([CH:19]=2)=[N:6][C:7]2[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=2[CH:13]=3)[CH2:34]1

Participants

3

Reactant 2

HCID 111970267,8-Difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidHCID 194236433-Amino-3-ethylazetidine dimethanesulphonate

Product 1

HCID 19423732HCID 19423732, compoundYield 68.9%

Procedure

8-(3-Amino-3-ethyl-1-azetidinyl)-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3carboxylic acid was prepared under the conditions of Example 15, but starting with 1.66 g of 7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 3.1 g of 3-amino-3-ethylazetidine dimethane-sulphonate. 1.46 g of 8-(3-amino-3-ethyl-1-azetidinyl)-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid, which decomposes at 294° C.

Workup

  1. custom8-(3-Amino-3-ethyl-1-azetidinyl)-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3carboxylic acid was prepared under the conditions of Example 15

Sources & evidence

ORD record
ord-f59f4a82baf7439ba32eef2321dea023
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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