Ethanol → Ethyl 6-fluoro-7-(3-trifluoroacetylamino-1-pyrrolidinyl)-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylate

HRID 851091Notes

Reaction equation

HRID 851091 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]([NH:5][CH:6]1[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:4].C(O)C.Cl[C:17]1[N:26]=[C:25]2[C:20]([C:21](=[O:34])[C:22]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][N:24]2[CH:27]=[CH2:28])=[CH:19][C:18]=1[F:35]>C(N(CC)CC)C>[F:35][C:18]1[CH:19]=[C:20]2[C:25](=[N:26][C:17]=1[N:8]1[CH2:9][CH2:10][CH:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:11])[F:12])[CH2:7]1)[N:24]([CH:27]=[CH2:28])[CH:23]=[C:22]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:21]2=[O:34]

Participants

5

Reactant 3

HCID 702EthanolHCID 5375752,2,2-Trifluoro-N-(pyrrolidin-3-YL)acetamideHCID 13135046Ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylate

Product 1

HCID 13135050Ethyl 6-fluoro-7-(3-trifluoroacetylamino-1-pyrrolidinyl)-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylateYield 84.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 3-trifluoroacetylaminopyrrolidine (5.46 g), ethanol (60 ml) and triethylamine (3 g) was added to ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylate (5.93 g) obtained according to Reference Example 1. The mixture was heated under reflux for one hour. After ice-cooling, the resulting crystals were collected by filtration and washed with ethanol. Recrystallization of the crude crystals from ethanol-chloroform gave 7.5 g of ethyl 6-fluoro-7-(3-trifluoroacetylamino-1-pyrrolidinyl)-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylate, m.p. 280°-282° C. A solution of the compound (4.4 g) thus obtained in 1 N sodium hydroxide (80 ml) was stirred for 2 hours at 60° C. At the same temperature the mixture was adjusted to pH 7-8 by addition of acetic acid. After ice-cooling, the resulting crystals were collected by filtration, washed with water, and dissolved in hot 10% acetic acid, followed by treating with charcoal.

Workup

  1. customobtained
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for one hour
  4. temperatureAfter ice-cooling
  5. filtrationthe resulting crystals were collected by filtration
  6. washwashed with ethanol
  7. customRecrystallization of the crude crystals from ethanol-chloroform

Sources & evidence

ORD record
ord-4fddc8299a6b44ee98ccf701a7c0226c
Source dataset
uspto-grants-1983_05
Patent number
US04382937

Reaction notes

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