Triethylamine → 7-[3-(Acetylamino)-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 1759551Notes

Reaction equation

HRID 1759551 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.[C:26]([NH:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)(=[O:28])[CH3:27]>C(#N)C>[C:26]([NH:29][CH:30]1[CH2:34][CH2:33][N:32]([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])[CH2:31]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5227153-AcetamidopyrrolidineHCID 127908597-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 130411377-[3-(Acetylamino)-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acidYield 88.5%

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-acetylaminopyrrolidine (2.56 g), and acetonitrile (100 ml) was heated under reflux for 2 hours. The mixture was concentrated to dryness under reduced pressure. The residue was mixed with water, neutralized with acetic acid, and cooled. The precipitate was collected, washed successively with water and ethanol, and dried to give 3.2 g of 7-(3-acetylamino-1-pyrrolidinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, m.p. 283°-284° C., on recrystallization from dimethylformamide-ethanol.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe mixture was concentrated to dryness under reduced pressure
  4. additionThe residue was mixed with water
  5. temperaturecooled
  6. customThe precipitate was collected
  7. washwashed successively with water and ethanol
  8. customdried

Sources & evidence

ORD record
ord-0ba1eeedd9b940339497cb5e53dcbe98
Source dataset
uspto-grants-1982_07
Patent number
US04341784

Reaction notes

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