1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(1,4-Diazabicyclo[3.2.1]octan-4-yl)-1-ethyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 1589573Notes

Reaction equation

HRID 1589573 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:18])=[C:10](S(CC)(=O)=O)[N:11]=2)[C:6](=[O:19])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1)[CH3:2].Cl.Cl.[N:25]12[CH2:32][CH:29]([CH2:30][CH2:31]1)[NH:28][CH2:27][CH2:26]2.N12CCCN=C1CCCCC2>C(#N)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:18])=[C:10]([N:28]3[CH:29]4[CH2:32][N:25]([CH2:31][CH2:30]4)[CH2:26][CH2:27]3)[N:11]=2)[C:6](=[O:19])[C:5]([C:20]([OH:22])=[O:21])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123740781,4-Diazabicyclo[3.2.1]octane dihydrochlorideHCID 135658501-Ethyl-7-ethanesulfonyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 4654527-(1,4-Diazabicyclo[3.2.1]octan-4-yl)-1-ethyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acidYield 18.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2.06 g (6.28 mmol) 1-ethyl-7-ethanesulfonyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid and 1.29 g (6.97 mmol) 1,4-diazabicyclo[3.2.1]octane dihydrochloride in 30 ml acetonitrile was treated with 3.10 g (20.4 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene. The resulting solution was stirred overnight and the precipitate which formed was filtered to afford 0.40 g of the title compound, mp 228°-229° C.

Workup

  1. customthe precipitate which formed
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-2dfce79dd8f940bf9a9a9ade3836b3d4
Source dataset
uspto-grants-1986_02
Patent number
US04571396

Reaction notes

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