Triethylamine → HCID 20531190, compound

HRID 1759556Notes

Reaction equation

HRID 1759556 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:19]([CH2:22][NH:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)(=[O:21])[CH3:20].C(N(CC)CC)C>C(O)C>[C:19]([CH2:22][NH:23][CH:24]1[CH2:28][CH2:27][N:26]([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])[CH2:25]1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 20531188HCID 20531188, compound

Product 1

HCID 20531190HCID 20531190, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (5.41 g), 3-(N-acetylmethylamino)pyrrolidine (4.26 g), triethylamine (6.06 g), and ethanol (100 ml) was heated under reflux for 2 hours with stirring. The reaction mixture was concentrated to dryness under reduced pressure. To the residue was added water (70 ml) and acetic acid (15 ml). After cooling the mixture, the precipitate was collected, washed with water, and recrystallized from dimethylformamide. There were obtained 7.4 g of 7-[3-(N-acetylmethylamino)-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, m.p. 287°-289° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. additionTo the residue was added water (70 ml) and acetic acid (15 ml)
  5. temperatureAfter cooling the mixture
  6. customthe precipitate was collected
  7. washwashed with water
  8. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-ca12143bcb124046a0bfdf04350569f2
Source dataset
uspto-grants-1982_07
Patent number
US04341784

Reaction notes

Loading…