7,8-Difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid → HCID 19423673, compound

HRID 743654Notes

Reaction equation

HRID 743654 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.[CH3:32][C:33]1([NH:37][CH3:38])[CH2:36][NH:35][CH2:34]1>>[F:1][C:2]1[C:20]([N:35]2[CH2:36][C:33]([CH3:32])([NH:37][CH3:38])[CH2:34]2)=[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

Participants

3

Reactant 2

HCID 111970267,8-Difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidHCID 194237363-Methyl-3-(methylamino)azetidine dimethanesulphonate

Product 1

HCID 19423673HCID 19423673, compound

Procedure

7-Fluoro-1-methyl-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 1.45 g of 7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b]-[1,8]naphthyridine-3-carboxylic acid and 2.34 g of 3-methyl-3-(methylamino)azetidine dimethanesulphonate. The reaction mixture is heated for 1 and a half hours to approximately 90° C. 1.12 g of 7-fluoro-1-methyl-8-(3-methyl-3-methylamino-1-azetidinyl)-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 approximately 336° C.

Workup

  1. temperatureThe reaction mixture is heated for 1 and a half hours to approximately 90° C

Sources & evidence

ORD record
ord-7d6f0f5508794e00903aceff1c4a9a9c
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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