1-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine → HCID 19423654, compound

HRID 743640Notes

Reaction equation

HRID 743640 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.CS(O)(=O)=O.CS(O)(=O)=O.[NH2:36][CH:37]1[CH2:40][NH:39][CH2:38]1>>[NH2:36][CH:37]1[CH2:40][N:39]([C:15]2[C:16]([F:18])=[CH:17][C:10]3[C:11]([CH:14]=2)=[N:12][C:13]2[N:4]([CH:1]4[CH2:3][CH2:2]4)[CH:5]=[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:7](=[O:20])[C:8]=2[CH:9]=3)[CH2:38]1

Participants

3

Reactant 2

HCID 148533401-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 194238183-Aminoazetidine dimethanesulphonate

Product 1

HCID 19423654HCID 19423654, compoundYield 53.6%

Procedure

8-(3-Amino-1-azetidinyl)-1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydrobenzo-[b][1,8]naphthyridine was prepared under the conditions of Example 2, but starting with 1.7 g of 1-cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine and 1.88 g of 3-aminoazetidine dimethanesulphonate. After 1 recrystallization in 50 cm3 of ethanol, 1.05 g of 8-(3-amino-1-azetidinyl)-1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine are obtained in the form of a yellow solid, melting point 178°-180° C.

Workup

  1. custom8-(3-Amino-1-azetidinyl)-1-cyclopropyl-3-ethoxycarbonyl-7-fluoro-4-oxo-1,4-dihydrobenzo-[b][1,8]naphthyridine was prepared under the conditions of Example 2
  2. customAfter 1 recrystallization in 50 cm3 of ethanol

Sources & evidence

ORD record
ord-28556b1a080e444b89ebd8486f845947
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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