1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Ethyl-6-fluoro-1,4-dihydro-7-(3-methyl-3,8-diazabicyclo[3.2.1]oct-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid, hydrochloride

HRID 1589577Notes

Reaction equation

HRID 1589577 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:18].Cl.Cl.[CH3:21][N:22]1[CH2:28][CH:27]2[NH:29][CH:24]([CH2:25][CH2:26]2)[CH2:23]1.N12CCCN=C1CCCCC2>C(#N)C>[ClH:1].[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([CH:23]3[N:22]([CH3:21])[CH2:28][CH:27]4[NH:29][CH:24]3[CH2:25][CH2:26]4)[N:11]=2)[C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]1)[CH3:13]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 229243503-Methyl-3,8-diazabicyclo(3.2.1)octane--hydrogen chloride (1/2)

Product 1

HCID 1317145251-Ethyl-6-fluoro-1,4-dihydro-7-(3-methyl-3,8-diazabicyclo[3.2.1]oct-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid, hydrochlorideYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.54 g (2.0 mmol) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, 0.50 g (2.5 mmol) of 3-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride [P. A. Sturm, et al, J. Med. Chem., 17, 481 (1974)], 0.75 ml (5.0 ml) 1,8-diazabicyclo[5.4.0]undec-7-ene and 20 ml of acetonitrile was heated under reflux for 1.5 hours and stirred overnight at room temperature. The reaction mixture was filtered and the solid washed with ethanol to give 0.46 g of the title compound, mp>310°.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe solid washed with ethanol

Sources & evidence

ORD record
ord-47639faa56e44556a95573744392a9ba
Source dataset
uspto-grants-1986_02
Patent number
US04571396

Reaction notes

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