Triethylamine → 7-(3-Aminopyrrolidin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 1759555Notes

Reaction equation

HRID 1759555 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].C(N(CC)CC)C.[NH2:26][CH:27]1[CH2:31][CH2:30][NH:29][CH2:28]1>C(#N)C>[NH2:26][CH:27]1[CH2:31][CH2:30][N:29]([C:2]2[N:11]=[C:10]3[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]3[CH2:12][CH3:13])=[CH:4][C:3]=2[F:18])[CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1644013-AminopyrrolidineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 2089337-(3-Aminopyrrolidin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (2.7 g), triethylamine (1.01 g), 3-aminopyrrolidine (1.72 g), and acetonitrile (100 ml) was heated under reflux for 1.5 hours. After cooling the mixture, the resulting precipitate was collected and suspended in water (20 ml). The suspension was adjusted to pH 7.5-8.0 with acetic acid. The precipitate was collected, washed with water, and dried to yield 2.85 g of 7-(3-amino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, m.p. 259°-262° C. (decomp.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling the mixture
  4. customthe resulting precipitate was collected
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-6cb695a9a76c41d998c781a3dd0a901e
Source dataset
uspto-grants-1982_07
Patent number
US04341784

Reaction notes

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