7,8-Difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid → HCID 19423711, compound

HRID 743653Notes

Reaction equation

HRID 743653 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][CH:33]1[CH2:36][NH:35][C:34]1([CH3:38])[CH3:37]>>[NH2:32][CH:33]1[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)[C:34]1([CH3:38])[CH3:37]

Participants

3

Reactant 2

HCID 111970267,8-Difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidHCID 194237473-Amino-2,2-dimethylazetidine dimethanesulphonate

Product 1

HCID 19423711HCID 19423711, compoundYield 32.4%

Conditions

Temperature
100 °C

Procedure

(RS)-8-(3-Amino-2,2-dimethyl-1-azetidinyl)-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid was prepared under the conditions described in 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 2.33 g of 3-amino-2,2-dimethylazetidine dimethanesulphonate. The reaction mixture is heated with stirring to approximately 100° C. for 5 hours. 0.6 g of (RS)-8-(3-amino-2,2-dimethyl-1-azetidinyl)-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a yellow solid, which decomposes at 285° C.

Workup

  1. custom(RS)-8-(3-Amino-2,2-dimethyl-1-azetidinyl)-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid was prepared under the conditions
  2. temperatureThe reaction mixture is heated

Sources & evidence

ORD record
ord-41bc19cabf1c486f93bb86d604be5b5a
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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