1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Ethyl-6-fluoro-7-(3-methyl-3,8-diazaspiro[4.4]nonan-8-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 978505Notes

Reaction equation

HRID 978505 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH2:8][CH2:7][C:6]2([CH2:12][CH2:11][NH:10][CH2:9]2)[CH2:5]1.N12CCCN=C1CCCCC2.[CH2:24]([N:26]1[C:35]2[C:30](=[CH:31][C:32]([F:37])=[C:33](Cl)[N:34]=2)[C:29](=[O:38])[C:28]([C:39]([OH:41])=[O:40])=[CH:27]1)[CH3:25]>C(#N)C>[CH2:24]([N:26]1[C:35]2[C:30](=[CH:31][C:32]([F:37])=[C:33]([N:10]3[CH2:11][CH2:12][C:6]4([CH2:7][CH2:8][N:4]([CH3:3])[CH2:5]4)[CH2:9]3)[N:34]=2)[C:29](=[O:38])[C:28]([C:39]([OH:41])=[O:40])=[CH:27]1)[CH3:25]

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 134918062-Methyl-2,7-diazaspiro[4.4]nonane dihydrochloride

Product 1

HCID 4618851-Ethyl-6-fluoro-7-(3-methyl-3,8-diazaspiro[4.4]nonan-8-yl)-4-oxo-1,8-naphthyridine-3-carboxylic acidYield 53.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred suspension of 4.40 g (20.7 mmol) of 2-methyl-2,7-diazaspiro[4.4]nonane dihydrochloride in 200 ml acetonitrile was treated with 9.42 g (62 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene and 5.42 g (20 mmol) 1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid was added. After stirring 23 hours at room temperature the precipitated product was filtered, washed with acetonitrile and ether, and recrystallized from ethanol to afford 3.99 g of the title compound, mp 252°-254° C. (dec).

Workup

  1. additionwas added
  2. filtrationwas filtered
  3. washwashed with acetonitrile and ether
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7d5a92ab0fe84e59b07bf1c711f7e402
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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