1-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine → HCID 19423695, compound

HRID 743641Notes

Reaction equation

HRID 743641 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]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.Cl.Cl.[CH3:28][N:29]([CH3:34])[CH:30]1[CH2:33][NH:32][CH2:31]1>>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15]([N:32]5[CH2:33][CH:30]([N:29]([CH3:34])[CH3:28])[CH2:31]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 148533401-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 22121220N,N-dimethylazetidin-3-amine dihydrochloride

Product 1

HCID 19423695HCID 19423695, compoundYield 69.5%

Procedure

1-Cyclopropyl-8-(3-dimethylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions described in Example 4, but starting with 1.4 g of 1-cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine and 1.04 g of 3-(dimethylamino)azetidine dihydrochloride. After concentration of the combined organic extracts to dryness, the solid obtained is recrystallized in 40 cm3 of ethanol. 1.2 g of 1-cyclopropyl-8-(3-dimethylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine are obtained in the form of a yellow solid, melting point 225° C.

Workup

  1. custom1-Cyclopropyl-8-(3-dimethylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions
  2. customAfter concentration of the combined organic extracts to dryness, the solid obtained
  3. customis recrystallized in 40 cm3 of ethanol

Sources & evidence

ORD record
ord-73e3ffae535848a8b00f35ae9e664f7b
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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