7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid → HCID 13772732, compound

HRID 868031Notes

Reaction equation

HRID 868031 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].[CH2:19]([NH:21][CH2:22][CH:23]1[CH2:27][CH2:26][NH:25][CH2:24]1)[CH3:20]>C(#N)C>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([N:25]3[CH2:26][CH2:27][CH:23]([CH2:22][NH:21][CH2:19][CH3:20])[CH2:24]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 13491786Ethyl-pyrrolidin-3-ylmethyl-amine

Product 1

HCID 13772732HCID 13772732, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.00 g (3.69 mmole) of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-napthyridine-3-carboxylic acid, 100 ml acetonitrile and 1.42 g (11.08 mmole) of N-ethyl-3-pyrrolidinemethanamine were stirred for three days at room temperature. The reaction mixture was then filtered, and the precipitate washed with water, ethanol/ether (1:3), and finally with ether until dry to give 0.715 g of 1-ethyl-7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo-1,8-napthyridine-3-carboxylic acid, mp 229.5°-231.5° C.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washthe precipitate washed with water, ethanol/ether (1:3)
  3. dry with materialfinally with ether until dry

Sources & evidence

ORD record
ord-def11b2de00741edb33464b1b97867b7
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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