Triethylamine → Ethyl 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 851093Notes

Reaction equation

HRID 851093 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.Cl[C:15]1[N:24]=[C:23]2[C:18]([C:19](=[O:32])[C:20]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][N:22]2C=C)=[CH:17][C:16]=1[F:33].[OH-].[Na+]>C(Cl)(Cl)Cl.O>[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:15]2[N:24]=[C:23]3[C:18]([C:19](=[O:32])[C:20]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][NH:22]3)=[CH:17][C:16]=2[F:33])[CH2:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 1644013-AminopyrrolidineHCID 13135046Ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylate

Product 1

HCID 10403713Ethyl 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a cooled solution of 3-aminopyrrolidine (3.6 g) and triethylamine (4.2 g) in 100 ml of chloroform was added a solution of ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyridine-3-carboxylate (4.15 g) in 50 ml of chloroform over a period of 40 minutes with stirring. The reaction mixture was kept under ice-cooling for one hour and then stirred for 4 hours at room temperature. To this mixture was added a mixture of water (50 ml) and 2 N sodium hydroxide (20 ml). The chloroform layer was separated from the reaction mixture, washed with water, and dried over anhydrous sodium sulfate. The chloroform was distilled off and the residue was triturated with ethyl acetate (20 ml). The resulting solid was collected and recrystallized from ethyl acetate to give 3.9 g of ethyl 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (ethyl ester of the compound 1) m.p. 139°-141° C.

Workup

  1. temperaturecooling for one hour
  2. stirringstirred for 4 hours at room temperature
  3. additionTo this mixture was added
  4. customThe chloroform layer was separated from the reaction mixture
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe chloroform was distilled off
  8. customthe residue was triturated with ethyl acetate (20 ml)
  9. customThe resulting solid was collected
  10. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f318818464ee4700b41fd09f329638ce
Source dataset
uspto-grants-1983_05
Patent number
US04382937

Reaction notes

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