7,8-Difluoro-1-methoxy-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid → HCID 19423751, compound

HRID 743657Notes

Reaction equation

HRID 743657 reaction equation
[F:1][C:2]1[C:21](F)=[CH:20][C:5]2=[N:6][C:7]3[N:8]([O: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]([O: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]1

Participants

3

Reactant 2

HCID 148533437,8-Difluoro-1-methoxy-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acidHCID 19423730HCID 19423730, compound

Product 1

HCID 19423751HCID 19423751, compoundYield 68.3%

Procedure

8-(3-Amino-3-methyl-1-azetidinyl)-7-fluoro-1-methoxy-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3carboxylic acid was prepared under the conditions of Example 15, but starting with 1.53 g of 7,8-difluoro-1-methoxy-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3carboxylic acid and 2.22 g of 3-amino-3-methylazetidine dimethane-sulphonate. 1.27 g of 8-(3-amino-3-methyl-1-azetidinyl)-7-fluoro-1-methoxy-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid, which decomposes at 346° C.

Workup

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

Sources & evidence

ORD record
ord-ef60e238d08f419cbf253866c9df4995
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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