7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → 1-Ethyl-6-fluoro-7-{3-[(methylamino)methyl]pyrrolidin-1-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 978489Notes

Reaction equation

HRID 978489 reaction equation
Cl[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].[CH3:19][NH:20][CH2:21][CH:22]1[CH2:26][CH2:25][NH:24][CH2:23]1>C(#N)C>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:24]3[CH2:25][CH2:26][CH:22]([CH2:21][NH:20][CH3:19])[CH2:23]3)[N:11]=2)[C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8]1)[CH3:13]

Participants

4

Reactant 2

HCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 13491795N-Methyl-1-(pyrrolidin-3-yl)methanamine

Product 1

HCID 4835021-Ethyl-6-fluoro-7-{3-[(methylamino)methyl]pyrrolidin-1-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidYield 44.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.00 g (3.69 mmole) 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-napthyridine-3-carboxylic acid, 40 ml acetonitrile, and 1.27 g (11.08 mmole) N-methyl3-pyrrolidinemethanamine are stirred at room temperature for three days. The reaction was filtered and the precipitate dissolved in aqueous ammonium hydroxide at pH 11. The solution was filtered and the solvent removed at reduced pressure. The product was washed with 5 ml of water, 10 ml ethanol/ether (1:1), and finally with ether until dry to give 0.571 g of 1-ethyl-6-fluoro-1,4-dihydro-7-[3-[(methylamino)-methyl]-1-pyrrolidinyl]-4-oxo-1,8-naphthyridine-3-carboxylic acid, mp 251°-253° C.

Workup

  1. filtrationThe reaction was filtered
  2. dissolutionthe precipitate dissolved in aqueous ammonium hydroxide at pH 11
  3. filtrationThe solution was filtered
  4. customthe solvent removed at reduced pressure
  5. washThe product was washed with 5 ml of water, 10 ml ethanol/ether (1:1)
  6. dry with materialfinally with ether until dry

Sources & evidence

ORD record
ord-e00e0ffbc7164879ab0b7f4447348478
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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