1-Cyclopropyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid → 1-Cyclopropyl-7-fluoro-8-(3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

HRID 743664Notes

Reaction equation

HRID 743664 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15](F)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:20])[C:6]([C:21]([OH:23])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.Cl.Cl.[CH3:26][NH:27][CH:28]1[CH2:31][NH:30][CH2:29]1>>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15]([N:30]5[CH2:31][CH:28]([NH:27][CH3:26])[CH2:29]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:20])[C:6]([C:21]([OH:23])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 148533411-Cyclopropyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidHCID 22121158N-methylazetidin-3-amine dihydrochloride

Product 1

HCID 194236841-Cyclopropyl-7-fluoro-8-(3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidYield 55.1%

Conditions

Temperature
40 °C

Procedure

1-Cyclopropyl-7-fluoro-8-(3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid was prepared under the conditions of Example 11, but starting with 1.5 g of 1-cyclopropyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 1.13 g of 3-(methylamino)azetidine dihydrochloride. The reaction mixture is stirred for 1 hour at 40° C. 1 g of 1-cyclopropyl-7-fluoro-8-(3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a yellow solid, which decomposes at 262° C.

Workup

  1. custom1-Cyclopropyl-7-fluoro-8-(3-methylamino-1-azetidinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid was prepared under the conditions of Example 11

Sources & evidence

ORD record
ord-78f5990c8e8f4d8db02f6d1bf51d611e
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

Loading…