Ethyl 1-ethyl-7-(ethylsulfonyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate → HCID 20531187, compound

HRID 1759559Notes

Reaction equation

HRID 1759559 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:18])=[C:10](S(CC)(=O)=O)[N:11]=2)[C:6](=[O:19])[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4]1)[CH3:2].[C:25]([CH2:28][NH:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)(=[O:27])[CH3:26]>C(#N)C>[C:25]([CH2:28][NH:29][CH:30]1[CH2:34][CH2:33][N:32]([C:10]2[N:11]=[C:12]3[C:7]([C:6](=[O:19])[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[F:18])[CH2:31]1)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 13290776Ethyl 1-ethyl-7-(ethylsulfonyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylateHCID 20531188HCID 20531188, compound

Product 1

HCID 20531187HCID 20531187, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing ethyl 1-ethyl-7-ethylsulfonyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (1.78 g), 3-(N-acetylmethylamino)pyrrolidine (2.13 g), and acetonitrile (70 ml) was heated under reflux for 3 hours. After cooling the mixture, the resulting precipitate was collected and recrystallized from acetonitrile to yield 1.58 g of ethyl 7-[3-(N-acetylmethylamino)-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, m.p. 212°-213° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling the mixture
  4. customthe resulting precipitate was collected
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-be7e75c546f94653b2a148a13168719e
Source dataset
uspto-grants-1982_07
Patent number
US04341784

Reaction notes

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