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 868030Notes

Reaction equation

HRID 868030 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-methyl-3-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 witn 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), and finally witn ether
  6. customuntil dry

Sources & evidence

ORD record
ord-c01f92d9c3dc488281302e6edfd6ef57
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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